Ethyl bromopyruvate → HCID 136343490, compound

HRID 895539Notes

Reaction equation

HRID 895539 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6](=[S:8])[NH2:7].Br[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>>[CH2:15]([O:14][C:12]([C:11]1[N:7]=[C:6]([C:2]2[NH:1][CH:5]=[CH:4][N:3]=2)[S:8][CH:10]=1)=[O:13])[CH3:16]

Participants

3

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 185216481H-Imidazole-2-carbothioamide

Product 1

HCID 136343490HCID 136343490, compoundYield 57.1%

Conditions

Temperature
75 °C

Procedure

A mixture of 1H-Imidazole-2-carbothioic acid amide (200 mg, 1.57 mmol) and Ethyl bromopyruvate (340 mg, 1.57 mmol) is heated at 75° C. for about 5 hours. After the volatiles are evaporated in vacuo, the residue is partitioned between Ethyl acetate (40 mL) and aqueous NaHCO3 (10 ML). The organic layer is separated, washed with water, dried and concentrated. The residue is purified on a silica gel column with 3% MeOH in CH2Cl2 as eluent to give 200 mg of the titled compound. 1H NMR (CDCl3): δ 8.15 (s, 1H), 7.20 (br, 1H), 7.10 (br, 1H), 4.33 (q, 2H), 1.23 (t, 3H). LRMS calcd 223, found 224 (MH+).

Workup

  1. customAfter the volatiles are evaporated in vacuo
  2. customthe residue is partitioned between Ethyl acetate (40 mL) and aqueous NaHCO3 (10 ML)
  3. customThe organic layer is separated
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue is purified on a silica gel column with 3% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-ded8fbb6a2c443d98cb4d34ecda85d93
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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