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

HRID 1009027
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HRID 1009027 반응식
[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]
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매
2회

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온도
57.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eb8ee93d08944e4b9b6115fc7395764f
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07973051B2

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