Ethyl bromopyruvate → HCID 136343490、化合物

HRID 1594067ノート

反応式

HRID 1594067 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

HCID 136343490HCID 136343490、化合物収率 57.1%

反応条件

温度
75 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-97aaafc38b0e4a549f1249aed19433fc
出典データセット
uspto-grants-2007_11
特許番号
US07300945B2

反応ノート

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