Carbon Disulfide → HCID 178527790, compound

HRID 1388502Notes

Reaction equation

HRID 1388502 reaction equation
[C:1](=[S:3])=[S:2].Cl[C:5]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:6]=1[NH2:7].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:12][C:10]1[CH:11]=[CH:5][C:6]2[N:7]=[C:1]([SH:3])[S:2][C:8]=2[CH:9]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 111232,4-DichloroanilineHCID 11430Potassium Carbonate

Product 1

HCID 178527790HCID 178527790, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

91 g of carbon disulfide are added dropwise to a stirred suspension of 162 g of 2,4-dichloroaniline and 414 g of potassium carbonate in 1,000 ml of dimethylformamide at about 25°-30° C. in the course of 40 minutes, under a nitrogen atmosphere. The mixture is then warmed to an internal temperature of 150° C. in the course of 2 hours, and this temperature is maintained for 16 hours. The batch is cooled and filtered and the filtrate is largely freed from dimethylformamide. 600 ml of water are added to the residue which remains, the mixture is acidified and the product which precipitates is filtered off and dried. 187.6 g (93.2% of theory) of 6-chloro-2-mercaptobenzothiazole of melting point 258° C. are obtained.

Workup

  1. temperaturethis temperature is maintained for 16 hours
  2. temperatureThe batch is cooled
  3. filtrationfiltered
  4. addition600 ml of water are added to the residue which
  5. customthe product which precipitates
  6. filtrationis filtered off
  7. customdried

Sources & evidence

ORD record
ord-b176762e6e644d27b17548d6de8ba220
Source dataset
uspto-grants-1984_02
Patent number
US04431813

Reaction notes

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