Water → HCID 19386922, compound

HRID 2399319Notes

Reaction equation

HRID 2399319 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH2:15][NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])=[CH:9][C:8]=2[CH:23]=1)([O-:3])=[O:2].ClC1C=CC=C(C(OO)=[O:32])C=1.O.C(=O)([O-])O.[Na+]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]3([CH2:15][NH:16][C:17](=[O:22])[C:18]([F:21])([F:19])[F:20])[O:32][CH:9]3[C:8]=2[CH:23]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 193871406-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-2H-1-benzopyran

Product 1

HCID 19386922HCID 19386922, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-2H-1-benzopyran (0.5 g, 1.52 mmol) in dichloromethane (10 ml) at 0° C. was treated with m-chloroperbenzoic acid (70%, 0.45 g, 1.52 mmol). After stirring for sixteen hours at room temperature, water and sodium hydrogen carbonate were added and the organic phase separated and evaporated under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane/acetone (95/5), to give 0.43 g of 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-3,4-dihydro-3,4-epoxy-2H-1-benzopyran 1NMR (CDCl3): δ1.4 (s, 3H), 1.6 (s, 3H), 3.7 (dd,1H), 3.85 (s, 1H), 4.15 (dd, 1H), 6.70 (br.s, 1H), 6.95 (d, 1H), 8.2 (d, 1H), 8.30 (s, 1H).

Workup

  1. customthe organic phase separated
  2. customevaporated under reduced pressure
  3. customThe residue was chromatographed on silica gel
  4. washeluting with dichloromethane/acetone (95/5)

Sources & evidence

ORD record
ord-9ba163a4ba264966aa991ab4966470fe
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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