Water → HCID 70574177, compound

HRID 1388982Notes

Reaction equation

HRID 1388982 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 watertoluene. 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 watertoluene

Sources & evidence

ORD record
ord-4599fd214cee49afa537849fceb12f29
Source dataset
uspto-grants-1981_01
Patent number
US04243407

Reaction notes

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