Water → HCID 15027712, compound

HRID 345962Notes

Reaction equation

HRID 345962 reaction equation
[NH2:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7](=[O:15])[N:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]=2[S:4][C:3]=1[C:22]([O:24][CH3:25])=[O:23].P(Cl)(Cl)(Cl)=O.O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:5][N:6]([CH:16]=[N:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7](=[O:15])[N:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]=2[S:4][C:3]=1[C:22]([O:24][CH3:25])=[O:23])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 9841326HCID 9841326, compound

Product 1

HCID 15027712HCID 15027712, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution o 1.05 g of methyl 1-amino-4,5-dihydro-5-oxo-4-phenyl-thieno[2,3-c]isoquinoline-2-carboxylate in 20 ml of dimethylformamide was added 0.55 g of phosphorus oxychloride at room temperature, and the mixture was stirred for 30 minutes. The reaction mixture was poured into water, and neutralized with a saturated sodium bicarbonate aqueous solution, and precipitates were collected by a filtration. The precipitates were washed with water, and dried under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.09 g of the desired product as pale yellow crystals (eluent: n-hexane/chloroform=1/1).

Workup

  1. customprecipitates
  2. filtrationwere collected by a filtration
  3. washThe precipitates were washed with water
  4. customdried under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1f0b3869d0e940afb3182734aaf89c37
Source dataset
uspto-grants-1991_10
Patent number
US05059692

Reaction notes

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