2-Chloroaniline → HCID 178418395, compound

HRID 1388501Notes

Reaction equation

HRID 1388501 reaction equation
C(O[C:4]([S-:6])=[S:5])C.[Na+].Cl[C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11]>CN(C)C=O>[SH:6][C:4]1[S:5][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1

Participants

4

Reactant 2

HCID 72402-ChloroanilineHCID 23690437Sodium ethylxanthate

Product 1

HCID 178418395HCID 178418395, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 216.2 g of sodium ethylxanthate in 250 ml of dimethylformamide is added dropwise to a solution, heated to 140°-150° C., of 63.8 g of 2-chloroaniline in 150 ml of dimethylformamide in the course of one hour, under a nitrogen atmosphere. During this addition, the internal temperature is kept at 150° C. by removing some of the distillate. The reaction mixture is then subsequently stirred under reflux for about 12 hours, cooled to about 80° C. and stirred into 1.2 l of ice-water. The resulting cloudy solution is acidified and the 2-mercaptobenzothiazole which has precipitated is filtered off. After washing and drying, 79 g (94.6% of theory) of 2-mercaptobenzothiazole of melting point 179°-180° C. are obtained.

Workup

  1. additionDuring this addition
  2. customis kept at 150° C.
  3. customby removing some of the distillate
  4. temperatureunder reflux for about 12 hours
  5. stirringstirred into 1.2 l of ice-water
  6. customthe 2-mercaptobenzothiazole which has precipitated
  7. filtrationis filtered off
  8. washAfter washing
  9. customdrying

Sources & evidence

ORD record
ord-0ad5baa9712b4ae8b77cf6064bf0b912
Source dataset
uspto-grants-1984_02
Patent number
US04431813

Reaction notes

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