Thionyl Chloride → HCID 22464638, compound

HRID 1274841Notes

Reaction equation

HRID 1274841 reaction equation
O[CH2:2][CH2:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([CH3:19])=[C:12]([C:14](=[O:18])[N:15]([CH3:17])[CH3:16])[S:13][C:7]=2[N:6]=[CH:5]1.S(Cl)([Cl:22])=O>ClCCCl>[Cl:22][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([CH3:19])=[C:12]([C:14](=[O:18])[N:15]([CH3:17])[CH3:16])[S:13][C:7]=2[N:6]=[CH:5]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22464717HCID 22464717, compound

Product 1

HCID 22464638HCID 22464638, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

29.9 g (106 mM [sic]) of 3-(2-hydroxyethyl)-5-methyl-6-dimethylcarbamoylthieno [2,3-d]pyrimidin-4-one in 200 ml of 1,2-dichloroethane were heated to reflux (slow dissolution) and then 12.7 ml (175 mM [sic]) of thionyl chloride in 20 ml of 1,2-dichloroethane were added dropwise. After refluxing for 1 h, the reaction mixture was cooled and concentrated. The crude product was partitioned between methylene chloride and water at pH=9. Drying and concentration of the organic phase resulted in isolation of 44.1 g (83%) of product as a dark oil which was purified by column chromatography (silica gel, eluent ethyl acetate). 23.8 g (76%) of product were isolated with melting point 120-122° C.

Workup

  1. temperatureto reflux
  2. dissolution(slow dissolution)
  3. temperatureAfter refluxing for 1 h
  4. temperaturethe reaction mixture was cooled
  5. concentrationconcentrated
  6. customThe crude product was partitioned between methylene chloride and water at pH=9
  7. customDrying

Sources & evidence

ORD record
ord-315eb342961144b1b40358a42d46e4d7
Source dataset
uspto-grants-2000_12
Patent number
US06159962

Reaction notes

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