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

HRID 867935Notes

Reaction equation

HRID 867935 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7a6be7a4aa82440997e3d6a27ffdecf4
Source dataset
uspto-grants-1988_10
Patent number
US04777179

Reaction notes

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