Methyl isothiocyanate → 6-nitro-2,2-dimethyl-3-(N'-methylthioureido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

HRID 1655390Notes

Reaction equation

HRID 1655390 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH2:15][NH2:16])=[C:9]([N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[O:23])[C:8]=2[CH:24]=1)([O-:3])=[O:2].[CH3:25][N:26]=[C:27]=[S:28]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH2:15][NH:16][C:27]([NH:26][CH3:25])=[S:28])=[C:9]([N:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[O:23])[C:8]=2[CH:24]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 193870526-nitro-2,2-dimethyl-3-aminomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

Product 1

HCID 193870046-nitro-2,2-dimethyl-3-(N'-methylthioureido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyranYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-nitro-2,2-dimethyl-3-aminomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (0.5 g, 1.53 mmol) in dichloromethane (10ml) and methyl isothiocyanate (0.11 g, 1.5 mmol) was stirred at room temperature for twenty six hours. The solvent was evaporated, and the residue washed with diethyl ether to give 0.34 g of 6-nitro-2,2-dimethyl-3-(N'-methylthioureido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 225° C.

Workup

  1. customThe solvent was evaporated
  2. washthe residue washed with diethyl ether

Sources & evidence

ORD record
ord-11ec3f7aa921405ca4d3ed6b7e58fd83
Source dataset
uspto-grants-1993_10
Patent number
US05250547

Reaction notes

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