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Ethanol → HCID 178507684, compound

HRID 26405
Notes
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Reaction equation

HRID 26405 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.C([OH:12])C.C(OO)(=O)C>C(O)(=O)C>[NH2:1][C:2]1[N+:7]([O-:12])=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 6585Peracetic AcidHCID 674322,4-Diamino-6-chloropyrimidine

Product 1

HCID 178507684HCID 178507684, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
35 °C

Procedure

144.5 G. of 2,4-diamino-6-chloropyrimidine are suspended in 2000 ml. of ethanol. The suspension is warmed to 35° C. while stirring (about 15 minutes), the greater part of the material passing into solution. This mixture is then cooled down to 6°-8° C. and at this temperature there are added dropwise within 40 minutes 175 ml. of 40% peracetic acid in glacial acetic acid. After completion of the addition, the mixture is stirred at 6°-8° C. for a further 30 minutes. Thereafter, the mixture is left to warm up to room temperature, and stirred at this temperature for 3 hours. 2000 Ml. of petroleum ether are added, the mixture is stirred for 1 hour and then left to stand overnight. The separated precipitate is filtered off, back-washed with 200 ml. of petroleum ether and dried under reduced pressure, there being obtained 2,4-diamino-6-chloro-pyrimidine-3-oxide. Recrystallization yields analytically pure product having a melting point of 193° C.

Workup

  1. temperatureThis mixture is then cooled down to 6°-8° C. and at this temperature there
  2. additionare added dropwise within 40 minutes 175 ml
  3. additionAfter completion of the addition
  4. stirringthe mixture is stirred at 6°-8° C. for a further 30 minutes
  5. waitThereafter, the mixture is left
  6. temperatureto warm up to room temperature
  7. stirringstirred at this temperature for 3 hours
  8. stirringthe mixture is stirred for 1 hour
  9. waitleft
  10. waitto stand overnight
  11. filtrationThe separated precipitate is filtered off
  12. washback-washed with 200 ml
  13. dry with materialof petroleum ether and dried under reduced pressure, there

Sources & evidence

ORD record
ord-8e32e366e0bb464a9c23ca4d3634022b
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04150131

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes