Hydrochloric Acid → 5-[4-[(3-Hydroxymethyl-1-methyl-1H-1,2,4-triazol-5-yl)amino]butyl]-3-methyl-2-thiophenecarboxaldehyde

HRID 867935노트

반응식

HRID 867935 반응식
O1CC[O:3][CH:2]1[C:6]1[S:10][C:9]([CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:8][C:7]=1[CH3:16].C([O:20][CH2:21][C:22]([N:24]=[C:25]([N:28]([CH3:37])[N:29]=CC1C=CC=CC=1)SC)=O)(=O)C.Cl>C1(C)C=CC=CC=1>[OH:20][CH2:21][C:22]1[N:24]=[C:25]([NH:15][CH2:14][CH2:13][CH2:12][CH2:11][C:9]2[S:10][C:6]([CH:2]=[O:3])=[C:7]([CH3:16])[CH:8]=2)[N:28]([CH3:37])[N:29]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 129265204-[5-(1,3-Dioxolan-2-yl)-4-methyl-2-thienyl]-butanamineHCID 53735339Methyl N-[2-(acetyloxy)acetyl]-1-methyl-2-(phenylmethylene)hydrazinecarboximidothioate

생성물 1

HCID 129265195-[4-[(3-Hydroxymethyl-1-methyl-1H-1,2,4-triazol-5-yl)amino]butyl]-3-methyl-2-thiophenecarboxaldehyde수율 17.7%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 4-[5-(1,3-dioxolan-2-yl)-4-methyl-2-thienyl]-butanamine (2.73 g) and methyl N-[2-(acetoxy)acetyl]-1-methyl-2-(phenylmethylene)-hydrazinecarboximidothioate (3.38 g) was heated to 60° for 2 h. Toluene (20 ml) and 5N hydrochloric acid (12 ml) were added and the mixture stirred at room temperature for 18 h. The mixture was basified to pH 8, washed with toluene, basified to pH 10 and extracted with ethyl acetate. The extract was evaporated to give an oil which was purified by column chromatography on silica using 3:1 ethyl acetate:methanol as eluent to give the title compound as a pale yellow solid (0.6 g) m.p. 118°-121° (softens).

후처리

  1. temperaturewas heated to 60° for 2 h
  2. washwashed with toluene
  3. extractionextracted with ethyl acetate
  4. customThe extract was evaporated
  5. customto give an oil which
  6. customwas purified by column chromatography on silica using 3:1 ethyl acetate

출처 및 근거

ORD 기록
ord-7a6be7a4aa82440997e3d6a27ffdecf4
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04777179

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