Carbon Disulfide → HCID 21396355, compound

HRID 1439750Notes

Reaction equation

HRID 1439750 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[OH-].[K+].Br[CH:13](Br)[CH3:14].C(=O)(O)[O-].[Na+].[C:21](=[S:23])=[S:22]>CN(C)C=O>[CH3:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[N:4]=[C:21]1[S:23][CH2:14][CH2:13][S:22]1

Participants

7

Reactant 5

HCID 6348Carbon DisulfideHCID 72514-Chloro-2-toluidineHCID 112011,1-DibromoethaneHCID 14797Potassium HydroxideHCID 516892Sodium Bicarbonate

Product 1

HCID 21396355HCID 21396355, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

50.0 g of 2-methyl-4-chloroaniline were dissolved in 300 ml of dimethylformamide and 27.0 g of carbon disulphide and 23.0 g of potassium hydroxide powder (about 88% strength) were introduced at 5-10° C, with cooling. The mixture was stirred for a further 2 hours and the solution thus obtained was added slowly, with stirring, to a mixture of 200 ml of dimethylformamide, 68 g of dibromoethane and 31 g of sodium bicarbonate. The mixture was kept at 60° C for a further 3 hours and was concentrated in vacuo to half its volume. 300 ml of benzene were added and the whole was stirred into 2 liters of water. The benzene layer was separated off, washed with water, dried over potassium carbonate and fractionated in vacuo.

Workup

  1. temperaturewith cooling
  2. customthe solution thus obtained
  3. additionwas added slowly
  4. waitThe mixture was kept at 60° C for a further 3 hours
  5. concentrationwas concentrated in vacuo to half its volume
  6. addition300 ml of benzene were added
  7. stirringthe whole was stirred into 2 liters of water
  8. customThe benzene layer was separated off
  9. washwashed with water
  10. dry with materialdried over potassium carbonate

Sources & evidence

ORD record
ord-efa3a060e34c4204bda325787e5c7176
Source dataset
uspto-grants-1977_11
Patent number
US04060628

Reaction notes

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