Methanol → 2-Aminothiophene-3-carboxamide

HRID 269854

반응식

HRID 269854 반응식
O[CH:2]1[CH2:7]SC(O)C[S:3]1.[C:9]([CH2:11][C:12]([NH2:14])=[O:13])#[N:10].CO>O.C(N(CC)CC)C>[NH2:10][C:9]1[S:3][CH:2]=[CH:7][C:11]=1[C:12]([NH2:14])=[O:13]

참가 물질

6

반응물 3

HCID 887MethanolHCID 7898CyanoacetamideHCID 983301,4-Dithiane-2,5-diol

생성물 1

HCID 6994952-Aminothiophene-3-carboxamide수율 141.7%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8471Triethylamine용매

반응 조건

온도
37.5 °C

실험 절차

2,5-Dihydroxy-1,4-dithiane (76 g) and cyanoacetamide (84 g) were added to a mixture of methanol (180 mL), water (10 mL) and triethylamine (10 g). The resulting mixture was heated at 35-40° C. for about 30 minutes while stirring, and then heated to 50-60° C. for an additional 30 minutes with stirring. The reaction mixture was then cooled to room temperature and poured into a mixture of ice (100 g)/water (360 mL). A fine precipitate formed upon addition, which was filtered and dried overnight to give 100.6 g of the title compound as a pale gray powder ((M+H)+=143, M.P.=159.0-159.6° C.).

후처리

  1. temperatureheated to 50-60° C. for an additional 30 minutes
  2. stirringwith stirring
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. customA fine precipitate formed upon addition, which
  5. filtrationwas filtered
  6. customdried overnight

출처 및 근거

ORD 기록
ord-935fc3f083c445918b8be8fdace31fac
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449472B2

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