Hydrochloric Acid → HCID 14722395, compound

HRID 1031682Notes

Reaction equation

HRID 1031682 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][C:9]1[CH:22]=[C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[C:20]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:19][C:10]=1[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:12].[C:35]([O-])(=O)[CH3:36].[Na+].Cl>O.C(OCC)(=O)C>[C:1]([N:23]([C:21]1[C:20]([O:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:19][C:10]2[C:11](=[O:12])[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:35]([CH3:36])[O:8][C:9]=2[CH:22]=1)[S:24]([CH3:27])(=[O:26])=[O:25])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 10620577HCID 10620577, compound

Product 1

HCID 14722395HCID 14722395, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.55 ml of acetic anhydride was added to 850 mg of ethyl 2-(2-hydroxy-4-methylsulfonylamino-5-phenoxybenzoyl)acetate and 540 mg of sodium acetate. The mixture was stirred for 10 minutes at 110°-120° C. The reaction mixture was introduced into a mixture of 20 ml of ethyl acetate and 20 ml of water. The resulting mixture was adjusted to pH 2 with 2N hydrochloric acid. 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 residue was purified by a column chromatography (eluant: a 5 : 1 mixture of toluene and ethyl acetate) to obtain 550 mg (yield: 55.6%) of 7-(N-acetyl-N-methylsulfonylamino)-3-ethoxycarbonyl-2-methyl-6-phenoxy-4H-1-benzopyran-4-one.

Workup

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

Sources & evidence

ORD record
ord-a431ed6f23544814a75aebda73c6481c
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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