Hydrochloric Acid → 1-(4-Chlorophenyl)-1,6-dihydro-4-methyl-6-oxopyrimidine

HRID 25869Notes

Reaction equation

HRID 25869 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12](C(OCC)=O)=[C:11]([CH3:20])[N:10]=[CH:9]2)=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([CH3:20])[N:10]=[CH:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 21325499Ethyl 1-(4-chlorophenyl)-1,6-dihydro-4-methyl-6-oxopyrimidine-5-carboxylate

Product 1

HCID 213255211-(4-Chlorophenyl)-1,6-dihydro-4-methyl-6-oxopyrimidineYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Treatment of 2.93 g (10 mmole) of ethyl 1-(4-chlorophenyl)-1,6-dihydro-4-methyl-6-oxopyrimidine-5-carboxylate prepared as in Example 1 with either 20 ml of concentrated hydrochloric acid or a mixture of 10 ml of concentrated hydrochloric acid and 10 ml of acetic acid at reflux for 5 hours gives, after methylene chloride extraction and ethanol recrystallization, a 40-45% yield of 1-(4-chlorophenyl)-1,6-dihydro-4-methyl-6-oxopyrimidine, m.p. 177°-9° C.

Workup

  1. temperatureat reflux for 5 hours
  2. customgives
  3. extractionafter methylene chloride extraction and ethanol recrystallization

Sources & evidence

ORD record
ord-d88b09595b6242d9b8b414976bb232d9
Source dataset
uspto-grants-1979_04
Patent number
US04147528

Reaction notes

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