Water → HCID 19387252, compound

HRID 2399330Notes

Reaction equation

HRID 2399330 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].C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34].O>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][S:33]([CH3:32])(=[O:35])=[O:34])=[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

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 193870526-nitro-2,2-dimethyl-3-aminomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

Product 1

HCID 19387252HCID 19387252, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-nitro-2,2-dimethyl-3-aminomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (0.43 g, 1.31 mmol) and triethylamine (0.22 ml, 1.58 mmol) in dichloromethane (15 ml) was added methanesulfonylchloride (0.12 ml, 1.55 mol). The solution was stirred at room temperature for four hours, and then water was added. The organic phase was separated and evaporated under reduced pressure. The residue was washed with diethyl ether, affording 0.3 g of 6-nitro-2,2-dimethyl-3-(methanesulfonamido)methyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 195° C.

Workup

  1. customThe organic phase was separated
  2. customevaporated under reduced pressure
  3. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-25e9c06589d94859b2555406b87af5cf
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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