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Chloroform → 5-(3-Benzoylthioureidomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

HRID 4685
Notes
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Reaction equation

HRID 4685 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:14][CH2:15][C:16]1[C:17]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N+:35]([O-:37])=[O:36])[CH:30]=2)=[N:18][C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:20][C:21]=1[CH3:22].C(Cl)(Cl)Cl>CC(C)=O.O>[C:5]([NH:3][C:2](=[S:1])[NH:14][CH2:15][C:16]1[C:17]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N+:35]([O-:37])=[O:36])[CH:30]=2)=[N:18][C:19]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:20][C:21]=1[CH3:22])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6212ChloroformHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 201514135-Aminomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

Product 1

HCID 540990445-(3-Benzoylthioureidomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidineYield 81%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×
HCID 962WaterSolvent

Procedure

A mixture of ammonium thiocyanate (0.25 g) and benzoyl chloride (0.41 g) in acetone (20 ml) was refluxed for 2 hours, and 5-aminomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.9 g) in acetone (5 ml) was added thereto. After refluxing for 2 hours, the reaction mixture was poured into a mixture of chloroform (100 ml) and water (50 ml). The organic layer was separated, washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the resulting crystal was recrystallized from diisopropyl ether to give 5-(3-benzoylthioureidomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.1 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter refluxing for 2 hours
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe resulting crystal was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-bc3a3701e39b42c0a3d5a904d9d85908
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04727073

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes