Water → 5-Hydroxymethyl-2-(2-methylpropyl)thiazole

HRID 14054

反応式

HRID 14054 の反応式
[C:1](=[S:7])([NH2:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[CH:8]([CH:10](Cl)[C:11](OCC)=O)=[O:9].O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[OH:9][CH2:8][C:10]1[S:7][C:1]([CH2:2][CH:3]([CH3:5])[CH3:4])=[N:6][CH:11]=1

参加物

6

反応物 4

HCID 962WaterHCID 118030Ethyl (chloroformyl)acetateHCID 516892Sodium BicarbonateHCID 3034257Butanethioamide, 3-methyl-

生成物 1

HCID 210859775-Hydroxymethyl-2-(2-methylpropyl)thiazole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
95 °C

実験手順

Isovalerothioamide (6.0 g, 51 mmol) and ethyl formylchloroacetate (Heterocycles 32 (4), 693-701, (1991), 5.0 g, 33 mmol) are dissolved in dry DMF (20 mL), and heated to 95 degrees C. for 4 hours. The reaction is subsequently cooled to 0 degrees C., and cold water (50 mL) is added. The mixture is basified to pH=8 with solid sodium bicarbonate, then extracted with ether (3×35 mL). The combined organic extracts are washed with water, then saline and dried over magnesium sulfate, filtered, and concentrated. The residue is purified by flash chromatography (ethyl acetate/hexanes 4-10% elution) to give the desired product. NMR (CDCl3, 300 MHz) δ 8.27, 4.45-4.30, 3.70-3.50, 3.00-2.80, 2.30-2.10, 1.40-1.20, and 1.10-0.90.

後処理

  1. temperatureThe reaction is subsequently cooled to 0 degrees C
  2. extractionextracted with ether (3×35 mL)
  3. washThe combined organic extracts are washed with water
  4. dry with materialsaline and dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography (ethyl acetate/hexanes 4-10% elution)

出典と根拠

ORDレコード
ord-75f58f65667748a0a0f97a393217bc0e
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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