1-Propanol → n-Propyl 1,4,5,6-Tetrahydropyrimidine-5-carboxylate Hydrochloride

HRID 1681871Notes

Reaction equation

HRID 1681871 reaction equation
Cl.[NH:2]1[CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5][N:4]=[CH:3]1.S(Cl)([Cl:13])=O.[CH2:15](O)[CH2:16][CH3:17]>>[ClH:13].[NH:4]1[CH2:5][CH:6]([C:8]([O:10][CH2:15][CH2:16][CH3:17])=[O:9])[CH2:7][N:2]=[CH:3]1

Participants

4

Reactant 3

HCID 10311-PropanolHCID 24386Thionyl ChlorideHCID 703421841,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride

Product 1

HCID 45261147n-Propyl 1,4,5,6-Tetrahydropyrimidine-5-carboxylate HydrochlorideYield 56%

Procedure

1,4,5,6-Tetrahydropyrimidine-5-carboxylic acid hydrochloride (1.5 g, 9.1 mmol) was dissolved in 1-propanol (30 ml). To the mixture was added thionyl chloride (1.1 g, 9.1 mmol) and the solution was refluxed for 22 h. The solvent was evaporated in vacuo to dryness. The residue was crystallized from methanol/THF to give 1.06 g (56%) of white crystals, mp 128°-130° C. 300 MHz nmr indicated product. Microanalysis calc.: C 46.49, H 7.26, N 13.56, found: C 46.21, H 6.96, N 17.41.

Workup

  1. temperaturethe solution was refluxed for 22 h
  2. customThe solvent was evaporated in vacuo to dryness
  3. customThe residue was crystallized from methanol/THF

Sources & evidence

ORD record
ord-1ef97c7f63eb4aceb16ae05fb905f366
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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