Triethylamine → HCID 42633472、化合物

HRID 1009042ノート

反応式

HRID 1009042 の反応式
[CH3:1][C:2]1[CH:6]=[C:5]([S:7](=[O:10])(=[O:9])[NH2:8])[S:4][C:3]=1[CH2:11][CH2:12][O:13][C:14](=[O:16])[CH3:15].Cl[C:18](OC1C=CC=CC=1)=[O:19].C(N(CC)CC)C.[Br:34][C:35]1[S:39][C:38]([NH2:40])=[N:37][C:36]=1[CH3:41]>C(#N)C>[C:14]([O:13][CH2:12][CH2:11][C:3]1[S:4][C:5]([S:7]([NH:8][C:18](=[O:19])[NH:40][C:38]2[S:39][C:35]([Br:34])=[C:36]([CH3:41])[N:37]=2)(=[O:10])=[O:9])=[CH:6][C:2]=1[CH3:1])(=[O:16])[CH3:15]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 129543735-Bromo-4-methyl-1,3-thiazol-2-amineHCID 67273589HCID 67273589、化合物

生成物 1

HCID 42633472HCID 42633472、化合物収率 50.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
60 °C

実験手順

Acetic acid 2-(3-methyl-5-sulfamoyl-thiophen-2-yl)-ethyl ester (0.120 g, 0.456 mmol) was dissolved in 4.5 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.057 g, 1.00 eq.) and triethylamine (0.159 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1 h. 5-Bromo-4-methyl-thiazol-2-ylamine (0.088 g, 1.00 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 60° C. over night. Cooling, pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with brine, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, ethyl acetate/5% MeOH), followed by crystallization from ethyl acetate/heptane, yielded finally 0.089 g of the title compound as light brown solid.

後処理

  1. additionwas then added
  2. temperatureCooling
  3. additionpouring
  4. extractionice/NH4Cl, twofold extraction with ethyl acetate
  5. washwashing with brine
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  7. customfollowed by crystallization from ethyl acetate/heptane

出典と根拠

ORDレコード
ord-8f8c23eb95994c4d97d81d5ba567246f
出典データセット
uspto-grants-2011_07
特許番号
US07973051B2

反応ノート

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