Hydrogen Sulfide → 4′-Methyl[1,1′-biphenyl]-2-carbothioamide

HRID 636253Notes

Reaction equation

HRID 636253 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)#[N:2].[SH2:16]>CO.C(N(CC)CC)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)(=[S:16])[NH2:2]

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 1455122-Cyano-4'-methylbiphenyl

Product 1

HCID 217112744′-Methyl[1,1′-biphenyl]-2-carbothioamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

First, 2.00 g of 2-cyano4′-methyl-1,1′-biphenyl was dissolved in a mixture of 15 ml of methanol and 4.18 g of triethylamine, and hydrogen sulfide gas was bubbled thereinto at room temperature to the point of saturation. After keeping at room temperature for 3 days, the solution was kept at 50° C. for 6 hours. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate containing 1% hydrochloric acid. The organic layer was concentrated to give 2.18 g of 2-thiocarbamoyl-4′-methyl-1,1′-biphenyl. Yield, 92%; m.p., 111-115° C.; m/z, 227

Workup

  1. customwas bubbled
  2. customat room temperature
  3. waitthe solution was kept at 50° C. for 6 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. extractionthe residue was extracted with ethyl acetate containing 1% hydrochloric acid
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-742ed109208f4af59c03e7b67c5ddc29
Source dataset
uspto-grants-2001_02
Patent number
US06191289B1

Reaction notes

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