Water → Sarakalim

HRID 1655387Notes

Reaction equation

HRID 1655387 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH2:14][NH:15][OH:16])=[C:8]([N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[O:23])[C:7]=2[CH:24]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35].O>ClCCl.ClCCl.CC(C)=O>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:12])([CH3:13])[C:9]([CH2:14][N:15]([OH:16])[C:34](=[O:36])[CH3:35])=[C:8]([N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[O:23])[C:7]=2[CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 19386946HCID 19386946, compound

Product 1

HCID 10047015SarakalimYield 44.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

A solution of 6-trifluoromethyl-2,2-dimethyl-3-(hydroxyamino)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (0.48 g, 1.31 mmol) in dichloromethane (13 ml) was cooled to 0° C. and treated with triethylamine (0.18 ml, 1.31 mmol) and acetyl chloride (0.1 ml, 1.31 mmol), and stirred at 0° C. for 45 minutes. Water was added, and the organic layer separated, washed with water and dried, and evaporated to give a crude product. Chromatography on silica gel eluting with dichloromethane/methanol (95/5) gave an oil which was crystallized from ether to give 0.24 g of 6-trifluoromethyl-2,2-dimethyl-3-(N-hydroxyacetamido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 188° C.

Workup

  1. customthe organic layer separated
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customto give a crude product
  6. customwas crystallized from ether

Sources & evidence

ORD record
ord-13d241ec1da24160b239a06e373d3ced
Source dataset
uspto-grants-1993_10
Patent number
US05250547

Reaction notes

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