Phosphorus oxychloride → HCID 59854770, compound

HRID 2112771Notes

Reaction equation

HRID 2112771 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([N:13]1[C:18](=[O:19])[C:17]2[C:20]3[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[C:21]=3[S:22][C:16]=2[N:15]=[C:14]1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[N+](C)=[CH:42][Cl:43].[Cl-].CC([O-])=O.[Na+]>ClCCCl.ClCCl.CN(C=O)C>[CH2:6]([N:13]1[C:18](=[O:19])[C:17]2[C:20]3[CH2:26][CH2:25][C:24]([CH:23]=[O:27])=[C:42]([Cl:43])[C:21]=3[S:22][C:16]=2[N:15]=[C:14]1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 517045Sodium AcetateHCID 59854727HCID 59854727, compound

Product 1

HCID 59854770HCID 59854770, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

POCl3 (3.5 ml) was added slowly to a cold, dry DMF (2.3 ml). 3-Benzyl-2-(3,4,5-trimethoxyphenyl)-6,7-dihydro-3H,5H-benzo[4,5]thieno[2,3-d]pyrimidine-4,8-dione (compound No. 2) (0.5 g, 1.1 mmol) in 1,2-dichloroethane was added slowly to the Vilsmeier reagent and stirred at room temperature for three hours after which the reaction mixture was refluxed for 15 minutes. After stirring overnight at room temperature the reaction mixture was diluted with dichloromethane and neutralized with NaOAc-solution (12 g/100 ml). The product was extracted with dichloromethane (3×30 ml). Organic phase was washed with water and dried. The crude product was purified by flash chromatography. The yield was 0.45 g (82%).

Workup

  1. temperaturewas refluxed for 15 minutes
  2. stirringAfter stirring overnight at room temperature the reaction mixture
  3. extractionThe product was extracted with dichloromethane (3×30 ml)
  4. washOrganic phase was washed with water
  5. customdried
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-6be380e7dbcf4942b9b3870da77466ac
Source dataset
uspto-grants-2009_04
Patent number
US07524853B2

Reaction notes

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