Dimethylcarbamoyl Chloride → HCID 178484761, compound

HRID 1074141Notes

Reaction equation

HRID 1074141 reaction equation
[SH:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH3:13][N:14]([CH3:18])[C:15](Cl)=[O:16]>N1C=CC=CC=1>[CH3:13][N:14]([CH3:18])[C:15]([S:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1)=[O:16]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 178527829HCID 178527829, compound

Product 1

HCID 178484761HCID 178484761, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

In 50 ml of pyridine was dissolved 5.0 g (28.4 millimoles) of 2-mercapto-4-phenylimidazole, and 3.13 ml (34.1 millimoles) of N,N-dimethylcarbamoyl chloride was added to the solution and the mixture was heated at 70° C. for 3 hours. The reaction mixture was concentrated under reduced pressure, and 200 ml of water and 200 ml of chloroform were added to the concentrate to effect extraction. The chloroform layer was concentrated and the concentrate was recrystallized from ethanol to obtain 2.4 g (yield=34%) of intended 2-(N,N-dimethylcarbamoylthio)-4-phenylimidazole (compound No. 21) in the form of a colorless crystal.

Workup

  1. additionwas added to the solution
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and 200 ml of water and 200 ml of chloroform
  3. additionwere added to the
  4. concentrationconcentrate
  5. extractionextraction
  6. concentrationThe chloroform layer was concentrated
  7. customthe concentrate was recrystallized from ethanol

Sources & evidence

ORD record
ord-b4503e7433f24e7e80bcb5663df4e960
Source dataset
uspto-grants-1990_11
Patent number
US04973588

Reaction notes

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