Water → 3-formyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

HRID 1031678Notes

Reaction equation

HRID 1031678 reaction equation
[OH:1][C:2]1[CH:12]=[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:10]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:9][C:3]=1[C:4]([CH2:6][CH:7]=[O:8])=[O:5].[CH3:25]OC(OC)N(C)C.C(OCC)(=O)C.O>C1C=CC=CC=1.CN(C)C=O>[CH:7]([C:6]1[C:4](=[O:5])[C:3]2[CH:9]=[C:10]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][C:2]=2[O:1][CH:25]=1)=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 78373Dimethylformamide dimethyl acetalHCID 151079232-(2-Hydroxy-4-methylsulfonylamino-5-phenoxybenzoyl)acetaldehyde

Product 1

HCID 147224393-formyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-oneYield 50.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Procedure

25 g of 2-(2-hydroxy-4-methylsulfonylamino-5-phenoxybenzoyl)acetaldehyde was dissolved in 260 ml of benzene and 130 ml of N,N-dimethylformamide. Thereto was added 26 ml of N,N-dimethylformamide dimethylacetal. The mixture was stirred for 8 hours at room temperature. The reaction mixture was introduced into a mixture consisting of 200 ml of ethyl acetate and 200 ml of water. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting oily matter was purified by a column chromatography (eluant: a 20 : 1 mixture of toluene and ethyl acetate) to obtain 13 g (yield: 50.4%) of 3-formyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one.

Workup

  1. additionThe reaction mixture was introduced into a mixture
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe resulting oily matter was purified by a column chromatography (eluant
  7. additiona 20 : 1 mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-cf438d8943ad4266a4ec923102e1089f
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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