Thionyl Chloride → HCID 11243073, compound

HRID 325075Notes

Reaction equation

HRID 325075 reaction equation
O[CH2:2][CH2:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][C:12]=3[S:13][C:7]=2[N:6]=[CH:5]1.S(Cl)([Cl:21])=O>ClCCCl>[Cl:21][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][C:12]=3[S:13][C:7]=2[N:6]=[CH:5]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15453507HCID 15453507, compound

Product 1

HCID 11243073HCID 11243073, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

42.0 g (158 mmol) of 3,4,5,6,7,8-hexahydro-3-(2-hydroxy)ethyl-7-methylpyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-one in 240 ml of 1,2-dichloroethane was heated to reflux and then 12.7 ml (175 mmol) of thionyl chloride in 20 ml of 1,2-dichloroethane were added dropwise. After rafluxing for 2 h, the mixture was allowed to cool and was poured into ice/water. After partitioning between methylene chloride and water at pH=10, the aqueous phase was back-extracted with methylene chloride. The combined organic phases were dried and concentrated. The crude product (40 g) was recrystallized from 400 ml of isopropanol. 30.5 g (68%) of product with melting point 159-161° C. were isolated.

Workup

  1. temperatureto reflux
  2. temperatureto cool
  3. customAfter partitioning between methylene chloride and water at pH=10
  4. extractionthe aqueous phase was back-extracted with methylene chloride
  5. customThe combined organic phases were dried
  6. concentrationconcentrated
  7. customThe crude product (40 g) was recrystallized from 400 ml of isopropanol

Sources & evidence

ORD record
ord-4a572a58c99a434194cfe024540dcf62
Source dataset
uspto-grants-2001_04
Patent number
US06222034B1

Reaction notes

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