Thionyl Chloride → HCID 22707763, compound

HRID 1274993Notes

Reaction equation

HRID 1274993 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%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

10.5 g (37.6 mM [sic]) 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) and then 3.5 ml (48 mM [sic]) of thionyl chloride in 20 ml of 1,2-dichloroethane were added dropwise. After refluxing for 1 h, the reaction mixture was allowed to cool, and the solid was filtered off with suction and washed with 1,2-dichloroethane. The crude product was partitioned between methylene chloride and water at pH=9. The organic phase was dried and concentrated to isolate 9.3 g (83%) of product as a dark oil which slowly crystallized and is sufficiently pure for further reactions, melting point 94-96° C.

Workup

  1. temperatureto reflux
  2. dissolution(slow dissolution)
  3. temperatureAfter refluxing for 1 h
  4. temperatureto cool
  5. filtrationthe solid was filtered off with suction
  6. washwashed with 1,2-dichloroethane
  7. customThe crude product was partitioned between methylene chloride and water at pH=9
  8. customThe organic phase was dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4636f17d1b95404d8edb8d628b744435
Source dataset
uspto-grants-2000_12
Patent number
US06159981

Reaction notes

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