Methyl isothiocyanate → HCID 136381155, compound

HRID 264828Notes

Reaction equation

HRID 264828 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([CH3:18])[C:9](=[O:10])[CH2:8][C:7]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]=2[O:5]1.CC(C)([O-])C.[K+].[CH3:25][N:26]=[C:27]=[S:28]>CN(C)C=O>[OH:10][C:9]1[C:4]([CH2:3][O:2][CH3:1])([CH3:18])[O:5][C:6]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:7]=2[C:8]=1[C:27](=[S:28])[NH:26][CH3:25]

Participants

5

Reactant 3

HCID 11167Methyl isothiocyanateHCID 19037048HCID 19037048, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 136381155HCID 136381155, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 5 g of 3,4-dihydro-2-methoxymethyl-2-methyl-6-nitro-2H-1-benzopyran-3-one and 60 ml of dried N,N-dimethylformamide was added 2.5 g of potassium tertiary butoxide under nitrogen stream with stirring under ice-cooling and the mixture was stirred for 5 minutes. Then, 1.7 ml of methyl isothiocyanate in 3 ml of N,N-dimethylformamide was added to the mixture and it was stirred at 5° C. for 18 hours. Ice water was added to the mixture and it was washed with ether. A water layer was acidified to be hydrochloric acid and extracted with ether. After an organic layer was washed with water and dried, the solvent was distilled. The resultant residue was purified according to silica gel column chromatography (developing solution, hexane:AcOEt=3:1) to obtain 5.1 g of 3-hydroxy-2-methoxymethyl-N,2-dimethyl-6-nitro-2H-1-benzopyran-4-carbothioamide with a melting point of 139°-141° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 5 minutes
  3. stirringwas stirred at 5° C. for 18 hours
  4. washwas washed with ether
  5. extractionextracted with ether
  6. washAfter an organic layer was washed with water
  7. customdried
  8. distillationthe solvent was distilled
  9. customThe resultant residue was purified

Sources & evidence

ORD record
ord-c050094b27d34222b9dccf6af2b59a21
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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