Propane, 1-chloro-3-isocyanato- → 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-(3-chloropropylureido)-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole

HRID 581025Notes

Reaction equation

HRID 581025 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][CH2:19][CH2:20][CH2:21][N:22]=[C:23]=[O:24]>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][CH2:21][CH2:20][CH2:19][Cl:18])=[O:24])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3

Participants

4

Reactant 2

HCID 166752Propane, 1-chloro-3-isocyanato-HCID 11107308(+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

Product 1

HCID 146277057,8-dihydro-6,6-dimethyl-7-hydroxy-8-(3-chloropropylureido)-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazoleYield 41.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

400 mg (1.70 mmol) of 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole and 40 ml of dichloromethane were stirred at room temperature, and 192 μl (1.87 mmol) of 3-chloropropyl isocyanate were added thereto and stirred for 5 hours. The crystals precipitated were taken out by filtration to obtain 250 mg of the intended compound as pale yellow crystals. (yield: 41%)

Workup

  1. customThe crystals precipitated
  2. filtrationwere taken out by filtration

Sources & evidence

ORD record
ord-20e57510682540d49921d8e5286cf9b6
Source dataset
uspto-grants-1999_07
Patent number
US05919806

Reaction notes

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