Glyoxal → HCID 20387450, compound

HRID 46480Notes

Reaction equation

HRID 46480 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:16][CH3:17])=[S:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:20]([CH:22]=[O:23])=[O:21].NC(N)=S>COCCOC.C(N(CC)CC)C>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([N:13]2[CH:20]([OH:21])[CH:22]([OH:23])[N:16]([CH3:17])[C:14]2=[S:15])[CH:4]=[C:3]([C:2]([F:19])([F:18])[F:1])[CH:8]=1

Participants

6

Reactant 3

HCID 7860GlyoxalHCID 2723790ThioureaHCID 2809071HCID 2809071, compound

Product 1

HCID 20387450HCID 20387450, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

30.0 g of N-(3,5-bis-trifluoromethyl-phenyl)-N'-methyl-thiourea were stirred in 100 ml of 1,2-dimethoxyethane and 10 ml of triethylamine, and then 22 g of a 30% strength aqueous glyoxal solution were added. The thiourea thereupon dissolved, the reaction being exothermic. The solution was stirred for a further 12 hours at 20° C. and was concentrated in vacuo and the residue was stirred with water and a little acetic acid. The reaction product, which had solidified, was filtered off, washed and dried. Yield 32.0 g; melting point: 133°-135° C. after recrystallisation from toluene.

Workup

  1. concentrationwas concentrated in vacuo
  2. stirringthe residue was stirred with water
  3. filtrationwas filtered off
  4. washwashed
  5. customdried
  6. custommelting point: 133°-135° C. after recrystallisation from toluene

Sources & evidence

ORD record
ord-526abb184c32425ebfdec52c5902cc93
Source dataset
uspto-grants-1979_11
Patent number
US04173645

Reaction notes

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