Trichloroacetyl isocyanate → 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-trichloroacetylureido-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole

HRID 581024Notes

Reaction equation

HRID 581024 reaction equation
[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH2:15])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3.[Cl:18][C:19]([Cl:26])([Cl:25])[C:20]([N:22]=[C:23]=[O:24])=[O:21]>ClCCl>[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH:15][C:23]([NH:22][C:20](=[O:21])[C:19]([Cl:26])([Cl:25])[Cl:18])=[O:24])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 11107308(+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

Product 1

HCID 146277037,8-dihydro-6,6-dimethyl-7-hydroxy-8-trichloroacetylureido-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazoleYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg (0.850 mmol) of 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole and 20 ml of dichloromethane were stirred at room temperature, and 100 μl (0.935 mmol) of trichloroacetyl isocyanate were added thereto and stirred for 5 hours. The crystals precipitated were filtered off to obtain 90 mg of the intended compoundas colorless crystals. (yield: 25%)

Workup

  1. customThe crystals precipitated
  2. filtrationwere filtered off
  3. customto obtain 90 mg of the intended compoundas colorless crystals

Sources & evidence

ORD record
ord-38b576da6da547f28590899780267b1e
Source dataset
uspto-grants-1999_07
Patent number
US05919806

Reaction notes

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