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

HRID 1199411Notes

Reaction equation

HRID 1199411 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

To a mixture of 200 mg (0.850 m mol) 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 added 68 mg (0.935 m mol) of methylisothiocyanate with stirring at the room temperature, followed by stirring for 23 hours. The precipitated crystals were separated by filter to obtain 122 mg of the intended compound as colorless crystals. (yield: 47%)

Workup

  1. stirringby stirring for 23 hours
  2. customThe precipitated crystals were separated
  3. filtrationby filter

Sources & evidence

ORD record
ord-050e566bbf8f4e23b32fe78d519f4b6b
Source dataset
uspto-grants-1990_02
Patent number
US04900752

Reaction notes

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