Methyl isothiocyanate → HCID 136381156, compound

HRID 264833Notes

Reaction equation

HRID 264833 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([CH2:18][O:19][CH3:20])[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.[CH3:21][N:22]=[C:23]=[S:24].CC(C)([O-])C.[K+]>CN(C)C=O>[OH:10][C:9]1[C:4]([CH2:18][O:19][CH3:20])([CH2:3][O:2][CH3:1])[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:23](=[S:24])[NH:22][CH3:21]

Participants

5

Reactant 3

HCID 11167Methyl isothiocyanateHCID 19037055HCID 19037055, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 136381156HCID 136381156, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5.1 g of 3,4-dihydro-2,2-bis(methoxymethyl)-6-nitro-2H-1-benzopyran-3-one and 60 ml of dried N,N-dimethylformamide was added 1.35 ml of methyl isothiocyanate under nitrogen stream with stirring under ice-cooling. Subsequently, 2.2 g of potassium tertiary butoxide was added therein. The mixture was stirred for 15 minutes and then further stirred at 5° C. for 11 hours. Ice water was added therein and the resultant reaction solution was washed with ether. A water layer was acidified to be hydrochloric acid and it was extracted with ether. An organic layer was washed with water and dried, and the solvent was distilled. The obtained residue was purified according to silica gel column chromatography (developing solution, MeOH:CH2Cl2 =2:98) to obtain 2.8 g of 3-hydroxy-2,2-bis(methoxymethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carbothioamide with a melting point of 97°-101° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 15 minutes
  3. stirringfurther stirred at 5° C. for 11 hours
  4. customthe resultant reaction solution
  5. washwas washed with ether
  6. extractionwas extracted with ether
  7. washAn organic layer was washed with water
  8. customdried
  9. distillationthe solvent was distilled
  10. customThe obtained residue was purified

Sources & evidence

ORD record
ord-a6e17b5e6861475799bf726fac334a97
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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