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

HRID 867935ノート

反応式

HRID 867935 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7a6be7a4aa82440997e3d6a27ffdecf4
出典データセット
uspto-grants-1988_10
特許番号
US04777179

反応ノート

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