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Acetic Acid → 2-[(4-Chlorophenylthio)methylamino]-4-methoxy-6-methylpyrimidine

HRID 34862
Notes
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Reaction equation

HRID 34862 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1.C=O.[C:21](O)(=O)C>CO>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH2:21][NH:1][C:2]2[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=2)=[CH:14][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 7815p-ChlorothiophenolHCID 5872364-Methoxy-6-methylpyrimidin-2-amine

Product 1

HCID 230432342-[(4-Chlorophenylthio)methylamino]-4-methoxy-6-methylpyrimidine

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

Procedure

A mixture of 13.99 g of 2-amino-4-methoxy-6-methylpyrimidine (0.1 mole), 14.8 g of 4-chlorothiophenol (0.1 mole), 9.4 g of aqueous 35% formaldehyde (0.11 mole) and 1 g of acetic acid are heated under reflux for 1 hour in 100 ml of methanol. The resultant solution is clarified by filtration, diluted with 150 ml of toluene and then the solvent is removed in a rotary evaporator. The residue crystallises after standing for some time. The melting point is 78°-82° after recrystallisation from hexane. The yield is 24 g (81% of theory).

Workup

  1. temperatureare heated
  2. filtrationThe resultant solution is clarified by filtration
  3. additiondiluted with 150 ml of toluene
  4. customthe solvent is removed in a rotary evaporator
  5. customThe residue crystallises
  6. customThe melting point is 78°-82° after recrystallisation from hexane

Sources & evidence

ORD record
ord-f56531faf056450bba8134dfded76144
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04764203

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes