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Triethylamine → N-[(5-bromo-4-ethyl-1,3-thiazol-2-yl)carbamoyl]-5-methylthiophene-3-sulfonamide

HRID 1009027
ノート
印刷プレビュー

反応式

HRID 1009027 の反応式
[CH3:1][C:2]1[S:6][CH:5]=[C:4]([S:7]([NH2:10])(=[O:9])=[O:8])[CH:3]=1.Cl[C:12](OC1C=CC=CC=1)=[O:13].C(N(CC)CC)C.[Br:28][C:29]1[S:33][C:32]([NH2:34])=[N:31][C:30]=1[CH2:35][CH3:36]>C(#N)C>[Br:28][C:29]1[S:33][C:32]([NH:34][C:12]([NH:10][S:7]([C:4]2[CH:3]=[C:2]([CH3:1])[S:6][CH:5]=2)(=[O:9])=[O:8])=[O:13])=[N:31][C:30]=1[CH2:35][CH3:36]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 572350435-Methylthiophene-3-sulfonamideHCID 665201935-Bromo-4-ethylthiazol-2-amine

生成物 1

HCID 42633277N-[(5-bromo-4-ethyl-1,3-thiazol-2-yl)carbamoyl]-5-methylthiophene-3-sulfonamide

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒
2 回

反応条件

温度
57.5 °C

実験手順

5-Methyl-thiophene-3-sulfonic acid amide (0.0496 g, 0.28 mmol) was dissolved in 1.5 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.0443 g, 1.01 eq.) and triethylamine (0.097 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1.25 h. The above prepared 5-bromo-4-ethyl-thiazol-2-ylamine (0.061 g, 1.05 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 55-60° C. over night. Cooling, pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, MeOH/ethyl acetate=1/99), yielded eventually, after precipitation from ethyl acetate/heptane, 0.038 g of the title compound as off-white solid.

後処理

  1. additionwas then added
  2. temperatureCooling
  3. additionpouring
  4. extractionice/NH4Cl, twofold extraction with ethyl acetate
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  7. customyielded eventually
  8. customafter precipitation from ethyl acetate/heptane, 0.038 g of the title compound as off-white solid

出典と根拠

ORDレコード
ord-eb8ee93d08944e4b9b6115fc7395764f
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07973051B2

反応ノート

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