Thionyl Chloride → HCID 22464638, compound

HRID 1935471Notes

Reaction equation

HRID 1935471 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 138.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

29.9 g (106 mmol) 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), after which 12.7 ml (175 mmol) of thionyl chloride in 20 ml of 1,2-dichloroethane were added dropwise. After 1 h of reflux boiling, the reaction mixture was evaporated after it had been cooled down. The crude product was partitioned between methylene chloride and water at pH=9. After the organic phase had been dried and evaporated, 44.1 g (83%) of product were isolated as a dark oil, which was purified by column chromatography (silica gel, eluent ethyl acetate). 23.8 g (76%) of product, having a m.p. of 120-122° C., were isolated.

Workup

  1. temperatureto reflux
  2. dissolution(slow dissolution)
  3. customthe reaction mixture was evaporated after it
  4. temperaturehad been cooled down
  5. customThe crude product was partitioned between methylene chloride and water at pH=9
  6. customAfter the organic phase had been dried
  7. customevaporated

Sources & evidence

ORD record
ord-55d48daf661d4c759d790d07ccc1479a
Source dataset
uspto-grants-2002_05
Patent number
US06387912B1

Reaction notes

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