Thiourea → HCID 23502821, compound

HRID 1835364Notes

Reaction equation

HRID 1835364 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:6][N:7]([CH3:27])[C:8](=[O:26])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([C:22](=O)[CH2:23]Br)=[N:11][CH:10]=1.[NH2:37][C:38]([NH2:40])=[S:39]>C(O)C>[NH2:40][C:38]1[S:39][CH:23]=[C:22]([C:12]2[CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH3:21])[C:9]([C:8]([N:7]([CH2:6][C:5]3[CH:28]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:30]=[C:3]([C:2]([F:36])([F:35])[F:1])[CH:4]=3)[CH3:27])=[O:26])=[CH:10][N:11]=2)[N:37]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 23502802HCID 23502802, compound

Product 1

HCID 23502821HCID 23502821, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 73 mg (0.13 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-bromoacetyl-N-methyl-4-o-tolyl-nicotinamide and 12 mg (0.15 mmol) thiourea in 1 ml ethanol was heated at reflux for 30 min. After cooling to room temperature the solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate. Washing with 1 M aqueous sodium hydroxide solution was followed by extraction of the aqueous layer with three portions of ethyl acetate. The combined organic layers were dried with sodium sulfate and concentrated. Column chromatography afforded 62 mg (88%) of the title compound as a light orange solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 min
  3. customwas evaporated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washWashing with 1 M aqueous sodium hydroxide solution
  6. extractionwas followed by extraction of the aqueous layer with three portions of ethyl acetate
  7. dry with materialThe combined organic layers were dried with sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-504b67574ad14daa9bab41a6dc555dc3
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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