Methyl isothiocyanate → 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-methylthioureido-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole

HRID 581023Notes

Reaction equation

HRID 581023 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.[CH3:18][N:19]=[C:20]=[S: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:20]([NH:19][CH3:18])=[S:21])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 11107308(+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

Product 1

HCID 146277217,8-dihydro-6,6-dimethyl-7-hydroxy-8-methylthioureido-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazoleYield 47%

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 68 mg (0.935 mmol) of methyl isothiocyanate were added thereto and stirred for 23 hours. The crystals precipitated were filtered off to obtain 122 mg of the intended compound as colorless crystals. (yield: 47%)

Workup

  1. customThe crystals precipitated
  2. filtrationwere filtered off

Sources & evidence

ORD record
ord-828cc3e108ae4dfebc186ce6c07693cd
Source dataset
uspto-grants-1999_07
Patent number
US05919806

Reaction notes

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