Dimethylformamide → HCID 59854770, compound

HRID 2375346Notes

Reaction equation

HRID 2375346 reaction equation
O=P(Cl)(Cl)Cl.CN(C=O)C.[CH2:11]([N:18]1[C:23](=[O:24])[C:22]2[C:25]3[CH2:31][CH2:30][CH2:29][C:28](=[O:32])[C:26]=3[S:27][C:21]=2[N:20]=[C:19]1[C:33]1[CH:38]=[C:37]([O:39][CH3:40])[C:36]([O:41][CH3:42])=[C:35]([O:43][CH3:44])[CH:34]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[N+](C)=[CH:47][Cl:48].[Cl-]>ClCCCl.ClCCl.CC([O-])=O.[Na+]>[CH2:11]([N:18]1[C:23](=[O:24])[C:22]2[C:25]3[CH2:31][CH2:30][C:29]([CH:28]=[O:32])=[C:47]([Cl:48])[C:26]=3[S:27][C:21]=2[N:20]=[C:19]1[C:33]1[CH:38]=[C:37]([O:39][CH3:40])[C:36]([O:41][CH3:42])=[C:35]([O:43][CH3:44])[CH:34]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 59854727HCID 59854727, compound

Product 1

HCID 59854770HCID 59854770, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 517045Sodium AcetateSolvent

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/l 00 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-5b53aab33c9542a4a7f8eab8f6b724ee
Source dataset
uspto-grants-2008_12
Patent number
US07465739B2

Reaction notes

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