US 12,466,799 B2
Method for producing N,N-disubstituted benzthiazolyl-sulfenamides
Holger Graf, Haan (DE); Melanie Wiedemeier-Jarad, Dormagen (DE); Jörg Hagemann, Cologne (DE); and Nele De Smet, Nieuwerkerken (BE)
Assigned to LANXESS Deutschland GmbH, Cologne (DE)
Appl. No. 17/605,301
Filed by LANXESS Deutschland GmbH, Cologne (DE)
PCT Filed Apr. 22, 2020, PCT No. PCT/EP2020/061175
§ 371(c)(1), (2) Date Oct. 21, 2021,
PCT Pub. No. WO2020/216780, PCT Pub. Date Oct. 29, 2020.
Claims priority of application No. 19171088 (EP), filed on Apr. 25, 2019.
Prior Publication US 2022/0213045 A1, Jul. 7, 2022
Int. Cl. C07D 277/80 (2006.01)
CPC C07D 277/80 (2013.01) 12 Claims
 
1. A method for preparing N, N-disubstituted benzothiazolylsulfenamides of the formula (I)

OG Complex Work Unit Chemistry
where R1, R2=each independently —CH(R3)(R4)
where R3, R4=each independently H, C3-alkyl,

OG Complex Work Unit Chemistry
and R5=C1-C3-alkyl,
y=0 to 2, and
n=0 to 5,
by reacting 2-mercaptobenzothiazole salts of the formula (II)

OG Complex Work Unit Chemistry
where Z=Na or K,
with amines of the formula (III)
NH(R1)(R2)  (III)
in which R1 and R2 have the definition above,
wherein the reaction is carried out in the presence of sodium hypochlorite at a pH of 10 to 12.