Triethylamine → HCID 23454953, compound

HRID 1680893Notes

Reaction equation

HRID 1680893 reaction equation
[CH:1]([NH:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.[CH3:19][N:20]([CH3:24])[C:21](Cl)=[S:22]>C(#N)C>[CH:1]([NH:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:21]([N:20]([CH3:24])[CH3:19])=[S:22])=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27871Dimethylthiocarbamoyl chlorideHCID 113189Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-

Product 1

HCID 23454953HCID 23454953, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

1-Formyl-2-(4-aminophenyl)hydrazine (1.51 g, 0.01 mole) and triethylamine (1.0 g, 0.01 mole) were mixed with dry acetonitrile (30 ml). The mixture was kept under a nitrogen atmosphere and a solution of dimethylthiocarbamoyl chloride (1.24 g, 0.01 mole) in acetonitrile (10 ml) was added dropwise at room temperature. After the addition was complete, the reaction mixture was chilled in ice, then filtered. The solid was washed with ethanol and allowed to dry. The material was stirred in water (40 ml) and heated to 60° C. to remove any hydrochloride salts. The aqueous mixture was filtered; the solid was washed with ether and dried. This gave 0.60 g (25 percent) of product as a pale tan powder, m.p. 187°-189° C.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was chilled in ice
  3. filtrationfiltered
  4. washThe solid was washed with ethanol
  5. customto dry
  6. customto remove any hydrochloride salts
  7. filtrationThe aqueous mixture was filtered
  8. washthe solid was washed with ether
  9. customdried

Sources & evidence

ORD record
ord-3be0a88b5b1045f6bfbd3d8df271bd5b
Source dataset
uspto-grants-1981_06
Patent number
US04276364

Reaction notes

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