Thionyl Chloride → HCID 22707763, compound

HRID 1935477Notes

Reaction equation

HRID 1935477 reaction equation
O[CH2:2][CH2:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]3[CH2:17][N:16]([CH2:18][CH3:19])[CH2:15][CH2:14][C:12]=3[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]3[CH2:17][N:16]([CH2:18][CH3:19])[CH2:15][CH2:14][C:12]=3[S:13][C:7]=2[N:6]=[CH:5]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22464549HCID 22464549, compound

Product 1

HCID 22707763HCID 22707763, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

10.5 g (37.6 mmol) of 3-(2-hydroxyethyl)-6-ethyl-3,4,5,6,7,8-hexahydropyrido[3′,4′:4,5]thieno[2,3-d]pyrimidin-4-one in 100 ml of 1,2-dichloroethane were heated to reflux (slow dissolution), after which 3.5 ml (48 mmol) of thionyl chloride in 20 ml of 1,2-dichloroethane were added dropwise. After 1 h of reflux boiling, the reaction mixture was allowed to cool down and the solid was filtered off with suction; it was then rewashed with 1,2-dichloroethane. The crude product was partitioned between methylene chloride and water at pH=9. After the organic phase had been dried and concentrated, 9.3 g (83%) of product were isolated as a dark oil, which slowly crystallizes throughout and which is sufficiently pure for the subsequent reactions, m.p. 94-96° C.

Workup

  1. temperatureto reflux
  2. dissolution(slow dissolution)
  3. temperatureto cool down
  4. filtrationthe solid was filtered off with suction
  5. customThe crude product was partitioned between methylene chloride and water at pH=9
  6. customAfter the organic phase had been dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8b42302ea10b44e990a424f29f26160f
Source dataset
uspto-grants-2002_05
Patent number
US06387912B1

Reaction notes

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