1-Benzothiophene-3-carbaldehyde → HCID 69429449, compound

HRID 1181793Notes

Reaction equation

HRID 1181793 reaction equation
[NH:1]([C:3]1[N:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5](=[O:15])[CH:4]=1)[NH2:2].[CH:16]1[CH:21]=[C:20]2[C:22]([CH:25]=O)=[CH:23][S:24][C:19]2=[CH:18][CH:17]=1>CO>[CH2:9]([N:8]1[C:3]([NH:1][N:2]=[CH:25][C:22]2[C:20]3[CH:21]=[CH:16][CH:17]=[CH:18][C:19]=3[S:24][CH:23]=2)=[CH:4][C:5](=[O:15])[N:6]([CH3:14])[C:7]1=[O:13])[CH:10]([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 2273281-Benzothiophene-3-carbaldehydeHCID 193560846-hydrazino-1-isobutyl-3-methyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 69429449HCID 69429449, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Hydrazino-1-isobutyl-3-methyl-2,4(1H,3H)-pyrimidinedione (1.2 g, 5.65 mmol) was dissolved in methanol (100 mL). To the yellow/brown solution was added thianaphthene-3-carboxaldehyde (917 mg, 5.65 mmol). A brown precipitate began to form after about 20 min. The mixture was stirred at room temperature for 3 h under nitrogen gas. HPLC showed complete formation of hydrazone (Rt=1.87 min, Kromasil, C8) The solvent was removed in vacuo and the brown slurry was pumped down to reveal a brown/yellow powder. Yield=1.85 g (92%), TLC, Rf=0.14 (CHCl3/MeOH); Rt:1.87 min. MS:357 (M+H)

Workup

  1. customto form after about 20 min
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-7472766f377c46a3b0143100e50e7090
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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