Water → 2-Carbamoyloxymethyl-6-methyl-4-(o-nitrophenyl)-3,5-diethoxycarbonyl-1,4-dihydropyridine

HRID 1995438Notes

Reaction equation

HRID 1995438 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]([CH3:28])=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].ClS([N:33]=[C:34]=[O:35])(=O)=O.O.C(OCC)(=O)C.CCCCCC>C1C=CC=CC=1>[NH2:33][C:34]([O:1][CH2:2][C:3]1[NH:4][C:5]([CH3:28])=[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 133883402-Hydroxymethyl-6-methyl-4-(nitrophenyl)-3,5-diethoxycarbonyl-1,4-dihydropyridineHCID 21226206Ethyl acetate hexane

Product 1

HCID 131315882-Carbamoyloxymethyl-6-methyl-4-(o-nitrophenyl)-3,5-diethoxycarbonyl-1,4-dihydropyridineYield 48.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Hydroxymethyl-6-methyl-4-(nitrophenyl)-3,5-diethoxycarbonyl-1,4-dihydropyridine (390 mg) was dissolved in benzene (10 ml), chlorosulfonyl isocyanate (0.2 ml) was added thereto, and the mixture was reacted under stirring at room temperature for 30 minutes. Water (10 ml) was added to the reaction mixture under cooling, and the mixture was stirred at room temperature for 30 minutes for hydrolysis. The reaction mixture thereby obtained was extracted with ethyl acetate, and the extracted solution was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane, whereupon crystals (210 mg, yield: 48.5%) were obtained.

Workup

  1. customthe mixture was reacted
  2. temperatureunder cooling
  3. stirringthe mixture was stirred at room temperature for 30 minutes for hydrolysis
  4. customThe reaction mixture thereby obtained
  5. extractionwas extracted with ethyl acetate
  6. concentrationthe extracted solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2163253c3466487aa99f28e255b60e05
Source dataset
uspto-grants-1983_09
Patent number
US04404378

Reaction notes

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