Imidazole → 2-Phenylethanethioamide

HRID 2120281Notes

Reaction equation

HRID 2120281 reaction equation
[NH:1]1C=CN=C1.[C:6]1([CH2:12][C:13](O)=[S:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N=C=NC(C)C)(C)C>CN(C=O)C>[C:6]1([CH2:12][C:13]([NH2:1])=[S:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 12734DiisopropylcarbodiimideHCID 178526157HCID 178526157, compound

Product 1

HCID 7313682-Phenylethanethioamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of amino acid methyl ester VI and imidazole in DMF, is added phenylthioacetic acid followed by diisopropylcarbodiimide at room temperature. The reaction mixture is stirred for 12 hours. After filtration on silica gel pad, the filtrate is poured into water and EtOAc. The organic layer is washed twice with water, dried over Na2SO4, and concentrated to afford α-phenylthioacetamide VII.

Workup

  1. filtrationAfter filtration on silica gel pad
  2. additionthe filtrate is poured into water and EtOAc
  3. washThe organic layer is washed twice with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3a41d5f021714c87a95f31b87e2b23f6
Source dataset
uspto-grants-2004_02
Patent number
US06689890B2

Reaction notes

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