Water → 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-2H-1-benzopyran

HRID 2399318Notes

Reaction equation

HRID 2399318 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[O:4].[H-].[Na+].[N+:10]([C:13]1[CH:14]=[CH:15][C:16]2[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH2:24]Br)=[CH:18][C:17]=2[CH:26]=1)([O-:12])=[O:11].O>CN(C)C=O.C(OCC)(=O)C>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]2[O:21][C:20]([CH3:22])([CH3:23])[C:19]([CH2:24][NH:5][C:3](=[O:4])[C:2]([F:7])([F:6])[F:1])=[CH:18][C:17]=2[CH:26]=1)([O-:12])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 67717TrifluoroacetamideHCID 193871046-nitro-2,2-dimethyl-3-bromomethyl-2H-1-benzopyran

Product 1

HCID 193871406-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-2H-1-benzopyranYield 32.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

2,2,2-trifluoroacetamide (0.53 g, 4.7 mmol) in dimethylformamide (2 ml) was added dropwise to a suspension of sodium hydride (80%, 1.4 g, 4.7 mmol) in dimethylformamide (2 ml). After one hour at room temperature 6-nitro-2,2-dimethyl-3-bromomethyl-2H-1-benzopyran (1.4 g, 4.7 mmol) was added and the mixture heated at 70° C. for eighteen hours. Water and ethyl acetate were added to the cooled solution and the organic phase separated and evaporated to give 0.51 g of 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-2H-1-benzopyran, 1NMR (CDCl3): δ1.5 (s, 6H), 4.15 (d, 2H), 6.25 (s, 1H), 6.85 (d, 1H), 6.9 (br.s), 1H), 7.85 (s, 1H), 8.05 (d, 1H).

Workup

  1. customthe organic phase separated
  2. customevaporated

Sources & evidence

ORD record
ord-1bbd4b2100f1452cb632c36ffc302c1d
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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