Sulfuryl chloride → 6-Chloro-2-benzothiazolamine

HRID 1284597Notes

Reaction equation

HRID 1284597 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[CH:4][CH:3]=1.S(Cl)(Cl)(=O)=O>ClC1C=CC=CC=1>[NH2:11][C:9]1[S:10][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=2[N:8]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 735843Thourea, (4-chlorophenyl)- (9CI)

Product 1

HCID 72266-Chloro-2-benzothiazolamineYield 85%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

186.5 parts of 4-chlorophenylthiourea were suspended with stirring in 850 parts of chlorobenzene, and 185 parts of sulfuryl chloride were added uniformly with stirring at a temperature of 40°-45° C. within about 3 hours. After the immediately starting gas development had ceased, the suspension formed which could be stirred with difficulty only was liberated from the chlorobenzene by steam distillation. The remaining suspension of 2-amino-6-chlorobenzothiazolium chloride was adjusted to pH 8 with 25% ammonia solution, thus causing the crude 2-amino-6-chlorobenzothiazole to agglomerate to a tacky mass. By decantation and drying, 146.3 parts of 2-amino-6-chlorobenzothiazole containing about 85% of pure product were obtained (=124.4 parts of 100% product, 67.4% of th.).

Workup

  1. additionwere added uniformly
  2. customthe suspension formed which
  3. stirringcould be stirred with difficulty
  4. distillationonly was liberated from the chlorobenzene by steam distillation
  5. additionThe remaining suspension of 2-amino-6-chlorobenzothiazolium chloride
  6. customBy decantation and drying

Sources & evidence

ORD record
ord-f5846bc2010e4544b29535946ac5f83e
Source dataset
uspto-grants-1986_01
Patent number
US04563533

Reaction notes

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