Hydrochloric Acid → HCID 178429334, compound

HRID 2285986Notes

Reaction equation

HRID 2285986 reaction equation
Cl.[Cl:2][CH2:3][C:4]([NH2:6])=[NH:5].[C:7](OC)(=[O:12])[CH2:8][C:9]([CH3:11])=O.[OH-].[Na+].Cl>CCOCC>[Cl:2][CH2:3][C:4]1[N:6]=[C:7]([OH:12])[CH:8]=[C:9]([CH3:11])[N:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 14798Sodium HydroxideHCID 27769572-Chloroacetamidine monohydrochloride

Product 1

HCID 178429334HCID 178429334, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Chloroacetamidine hydrochloride (6.45 g, 0.05 mole), methyl acetoacetate (6.38 g, 0.055 mole) and 2 N aqueous sodium hydroxide solution (50 ml) were mixed and stirred for 1 hour at room temperature. The reaction solution was acidified (pH 4-5) with 6 N hydrochloric acid, followed by extraction with chloroform. The chloroform extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a brown crystal. The crystal was stirred in ether and then filtered to obtain 5.1 g (64% of the theoretical yield) of 2-(chloromethyl)-4-hydroxy-6-methylpyrimidine as colorless plate-like crystals (m.p. 157°-159° C.).

Workup

  1. extractionfollowed by extraction with chloroform
  2. extractionThe chloroform extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain a brown crystal
  6. filtrationfiltered
  7. customto obtain 5.1 g (64% of the

Sources & evidence

ORD record
ord-de8eded8a22e4e0783ca29db7076b98f
Source dataset
uspto-grants-1982_04
Patent number
US04326058

Reaction notes

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