Water → HCID 67714130, compound

HRID 2259897Notes

Reaction equation

HRID 2259897 reaction equation
[OH:1][C:2]([CH3:19])([CH3:18])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH2:6][CH2:5]1.[CH3:20][C:21]1[C:26](=[O:27])[C:25]2[CH:28]=[CH:29][CH:30]=[C:31]([C:32]([Cl:34])=[O:33])[C:24]=2[O:23][C:22]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[OH-].[Na+].O>ClCCCl.ClCCl>[ClH:34].[ClH:34].[CH3:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:7]1[CH2:6][CH2:5][N:4]([CH2:3][C:2]([CH3:19])([O:1][C:32]([C:31]2[C:24]3[O:23][C:22]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[C:21]([CH3:20])[C:26](=[O:27])[C:25]=3[CH:28]=[CH:29][CH:30]=2)=[O:33])[CH3:18])[CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 13122092HCID 13122092, compoundHCID 19972666HCID 19972666, compound

Product 1

HCID 67714130HCID 67714130, compoundYield 111.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

5.29 g of Intermediate XXVIII in 25 ml of 1,2-dichloroethane was added dropwise at 60° C. to a solution of 6 g of 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carbonyl chloride in 22 ml of 1,2-dichloroethane. The reaction mixture was refluxed for 16 hours, and then cooled to ambient temperature and poured into cold 0.5N aqueous sodium hydroxide solution. Water and dichloromethane were added. The organic phase was separated off, washed with aqueous sodium chloride solution and dried on anhydrous sodium sulfate. The solvents were evaporated off and the oily residue was purified by flash chromatography on silica gel, eluting with petroleum ether:ethyl acetate (85:15). The collected fractions were evaporated to dryness in vacuo and the residue was dissolved in ethanol. Excess ethanolic hydrogen chloride was added to give 6.71 g of the title compound, m.p. 203°-204° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. customThe organic phase was separated off
  3. washwashed with aqueous sodium chloride solution
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvents were evaporated off
  6. customthe oily residue was purified by flash chromatography on silica gel
  7. washeluting with petroleum ether:ethyl acetate (85:15)
  8. customThe collected fractions were evaporated to dryness in vacuo
  9. dissolutionthe residue was dissolved in ethanol
  10. additionExcess ethanolic hydrogen chloride was added

Sources & evidence

ORD record
ord-66d19b27932c4cf7ac70d84b69338b9f
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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