Acetic Acid → HCID 15294391, compound

HRID 1653727Notes

Reaction equation

HRID 1653727 reaction equation
[CH3:1][C:2]1[NH:3][CH2:4][CH:5]([OH:8])[CH2:6][N:7]=1.S(Cl)(Cl)=O.[C:13](O)(=[O:15])[CH3:14]>>[CH3:1][C:2]1[NH:7][CH2:6][CH:5]([O:8][C:13](=[O:15])[CH3:14])[CH2:4][N:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24386Thionyl ChlorideHCID 20080447HCID 20080447, compound

Product 1

HCID 15294391HCID 15294391, compound

Procedure

2-Methyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine (JOC 1966, 31, 3838; 1.5 g, 13.3 mmol) was dissolved in glacial acetic acid (100 ml) with stirring, and thionyl chloride (1 ml, 13.1 mmol ) was added dropwise. The resulting solution was refluxed 19 hours, then evaporated to dryness in vacuo. The residue was taken up in water (5 ml), the pH adjusted to 9 (sat. Na2CO3), extracted with chloroform and the organics discarded. The aqueous layer was then adjusted to pH 12 (sat. NaOH) and extracted with chloroform. The chloroform was dried (MgSO4) and evaporated in vacuo to 575 mg (28%) white crystals, mp 141°-146° C. 400 MHz nmr confirmed the product calculated: C 53.82, H 7.75, N 17.94; found: C 53.9, H 7.73, N 17.77.

Workup

  1. temperatureThe resulting solution was refluxed 19 hours
  2. customevaporated to dryness in vacuo
  3. extractionextracted with chloroform
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform was dried (MgSO4)
  6. customevaporated in vacuo to 575 mg (28%) white crystals, mp 141°-146° C

Sources & evidence

ORD record
ord-c3f53e86984143b98959f4af8ac767ef
Source dataset
uspto-grants-1995_04
Patent number
US05403845

Reaction notes

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