Hydrochloric Acid → 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-sulfonyl chloride

HRID 1653781Notes

Reaction equation

HRID 1653781 reaction equation
N([O-])=O.[Na+].N[C:6]1[C:15]2[O:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([CH3:22])[C:11](=[O:23])[C:10]=2[CH:9]=[CH:8][CH:7]=1.[S:24](=[O:26])=[O:25].[ClH:27]>O.C(O)(=O)C>[CH3:22][C:12]1[C:11](=[O:23])[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:24]([Cl:27])(=[O:26])=[O:25])[C:15]=2[O:14][C:13]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 199728088-amino-3-methyl-4-oxo-2-phenyl-4H-1-benzopyranHCID 23668193Sodium Nitrite

Product 1

HCID 199727993-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-sulfonyl chloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Procedure

A solution of 4.55 g of sodium nitrite in 12 ml of water was added dropwise to a stirred mixture of 15.1 g of 8-amino-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran (prepared as described in Da Re, P. et al., Il. Farmaco (Ed. Sci.) 11: 670, 1956) in 150 ml of hydrochloric acid (d=1.18) at -5° C. Stirring was continued at 0° C. for 30 minutes. The solution was poured, over a period of 10 minutes and at -5° to 0° C., into 120 ml of a 30% by weight solution of sulfur dioxide in acetic acid containing 1.53 g of cupric chloride dihydrate and 13 ml of water. After 1 hour at 0° C. and 1 hour at 20°-25° C., 300 ml of iced water was added to the mixture. A precipitate formed and was collected by suction filtration, washed with water and dried in a desiccator over sodium hydroxide until of constant weight to give 18 g of crude title product, m.p. 165°-170° C., for use without further purification.

Workup

  1. waitAfter 1 hour at 0° C.
  2. customA precipitate formed
  3. filtrationwas collected by suction filtration
  4. washwashed with water
  5. dry with materialdried in a desiccator over sodium hydroxide until of constant weight

Sources & evidence

ORD record
ord-9bb13338a50d44bc9866e6a3a196b3c8
Source dataset
uspto-grants-1995_04
Patent number
US05403842

Reaction notes

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