Dimethylformamide → 2-Bromo-4-phenylthioaniline

HRID 1065946Notes

Reaction equation

HRID 1065946 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([S:9][C:10]#N)[CH:6]=[CH:5][C:3]=1[NH2:4].CN(C)C=O.[S-2].[Na+].[Na+].I[C:21]1[CH:26]=[CH:25]C=[CH:23][CH:22]=1>O>[Br:1][C:2]1[CH:8]=[C:7]([S:9][C:10]2[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=2)[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11575IodobenzeneHCID 14804Sodium SulfideHCID 38124212-Bromo-4-thiocyanatoaniline

Product 1

HCID 226212822-Bromo-4-phenylthioaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-bromo-4-thiocyanoaniline (91.6 g., 0.4 mole) and dimethylformamide is added dropwise to a solution of sodium sulfide (0.48 mole) and water, under nitrogen, and the resulting solution is heated at 50° C. for one hour. Cuprous oxide (34.33 g., 0.24 mole) and iodobenzene (97.9 g., 0.48 mole) are added and the mixture is heated at a heating bath temperature of 150° C. for 4.5 hours. The reaction is quenched with water, methylene chloride is added and the resulting mixture is filtered through filter aid to remove suspended solids. The aqueous and organic layers are separated, and the aqueous layer is extracted three times with methylene chloride. The methylene chloride extracts are combined, washed with water and dried. Removal of the drying agent and methylene chloride gives the desired product in 95% of the theoretical yield. A purified sample melts at 61°-63° C.

Workup

  1. temperaturethe mixture is heated at a heating bath temperature of 150° C. for 4.5 hours
  2. customThe reaction is quenched with water, methylene chloride
  3. additionis added
  4. filtrationthe resulting mixture is filtered
  5. filtrationthrough filter aid
  6. customto remove
  7. customThe aqueous and organic layers are separated
  8. extractionthe aqueous layer is extracted three times with methylene chloride
  9. washwashed with water
  10. customdried
  11. customRemoval of the drying agent and methylene chloride

Sources & evidence

ORD record
ord-75a6e46ef72e40aaa7ea081b7175049b
Source dataset
uspto-grants-1982_05
Patent number
US04331817

Reaction notes

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