Water → HCID 70574177, compound

HRID 224491Notes

Reaction equation

HRID 224491 reaction equation
O.Br[CH2:3][C:4](=O)[CH:5](C)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:7].[C:18]([NH:23][C:24]([NH2:26])=[S:25])(=[O:22])[CH:19]([CH3:21])[CH3:20].N1C=CC=C[CH:28]=1>C(O)C>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:6]([CH2:5][CH:4]=[C:3]2[CH2:28][S:25][C:24]([NH:23][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])=[N:26]2)=[O:7])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 3555130N-Carbamothioyl-2-methylpropanamideHCID 20297521HCID 20297521, compound

Product 1

HCID 70574177HCID 70574177, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 300 ml reaction flask fitted with a magnetic stirrer, heating mantle, thermometer and water-cooled condenser was charged with 5.0 g (0.016 mole) of 4-bromo-4'-chloro-2-methylacetoacetanilide [M.P. 103°-105°; prepared as described by Hodgkinson and Staskun in The Journal of Organic Chemistry, vol. 34, p. 1710 (1969)], 100 ml of ethanol, 2.5 g (0.017 mole) of N-isobutyrylthiourea [M.P. 112°-114°; prepared as described by Moore and Crossley in The Journal of the American Chemical Society, vol. 62, p. 3273 (1940)] and 1.6 g (0.02 mole) of pyridine. The solution was stirred and refluxed for three hours. The solvent was removed under reduced pressure and the residual solid was stirred with water-toluene. There was obtained 3.9 g (69%) of white solid, M.P. 202°-204°. N.M.R. (dimethyl-d6 sulfoxide)∂ 1.1-1.3 (2×CH3), 1.4- 1.6 (CH3, doublet), 3.5-4.0 (2×CH), 6.8 (hetero-aromatic), 7.2-7.7 (aromatic).

Workup

  1. customA 300 ml reaction flask
  2. customfitted with a magnetic stirrer
  3. temperatureheating mantle
  4. customprepared
  5. customprepared
  6. temperaturerefluxed for three hours
  7. customThe solvent was removed under reduced pressure
  8. stirringthe residual solid was stirred with water-toluene

Sources & evidence

ORD record
ord-ead4de0097254aa3ad8422de29bd42df
Source dataset
uspto-grants-1980_11
Patent number
US04232163

Reaction notes

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