Ethanol → 2-amino-4-[N-4-chlorophenyl-N-isopropyl (carbamoylethylidene)] thiazole

HRID 224500Notes

Reaction equation

HRID 224500 reaction equation
[CH:1]([N:4]([C:12](=[O:19])[CH:13](C)[C:14]([CH2:16]Br)=O)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[NH2:20][C:21]([NH2:23])=[S:22].[CH2:24](O)C>>[NH2:20][C:21]1[S:22][CH2:24][C:16](=[CH:14][CH2:13][C:12](=[O:19])[N:4]([C:5]2[CH:6]=[CH:7][C:8]([Cl:11])=[CH:9][CH:10]=2)[CH:1]([CH3:2])[CH3:3])[N:23]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 2723790ThioureaHCID 20297527N-isopropyl-4'-chloro-4-bromo-2-methylacetoacetanilide

Product 1

HCID 867373202-amino-4-[N-4-chlorophenyl-N-isopropyl (carbamoylethylidene)] thiazole

Procedure

A solution containing 43.3 g (0.13 mole) of N-isopropyl-4'-chloro-4-bromo-2-methylacetoacetanilide, 10.2 g (0.14 mole) of thiourea and 300 ml of ethanol was refluxed for two hours. A portion of the ethanol was evaporated and water was added. The reaction solution was made basic with ammonium hydroxide. After drying, the white solid weighed 33 g (78%), M.P. 145°-47°. N.M.R. (dimethyl-d6 sulfoxide, CDCl3) ∂0.9-1.3 (CH3, 9 protons), 3.1-3.4 (CH), 4.6-5.1 (CH, isopropyl), 5.9 (hetero-aromatic), 6.5 (NH2), 7.0-7.5 (aromatic).

Workup

  1. temperaturewas refluxed for two hours
  2. customA portion of the ethanol was evaporated
  3. additionwater was added
  4. customAfter drying

Sources & evidence

ORD record
ord-8271cec477264f0da7384850bf14938b
Source dataset
uspto-grants-1980_11
Patent number
US04232163

Reaction notes

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