2-Propanone, 1-nitro- → 4-(2-Benzylmercaptophenyl)-1,4-dihydro-2,6-dimethyl-5-nitropyridine-3-carboxylic acid N-[4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-phenyl]-amide

HRID 247368Notes

Reaction equation

HRID 247368 reaction equation
[CH2:1]([S:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:17]([CH2:20][C:21](=O)[CH3:22])([O-:19])=[O:18].[O:24]=[C:25]1[NH:30][N:29]=[C:28]([C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:43])/[CH:39]=[C:40](\[NH2:42])/[CH3:41])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1>C(O)(C)C>[O:24]=[C:25]1[NH:30][N:29]=[C:28]([C:31]2[CH:32]=[CH:33][C:34]([NH:37][C:38]([C:39]3[CH:11]([C:10]4[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=4[S:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:20]([N+:17]([O-:19])=[O:18])=[C:21]([CH3:22])[NH:42][C:40]=3[CH3:41])=[O:43])=[CH:35][CH:36]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 662962-Propanone, 1-nitro-HCID 111178092-(Benzylsulfanyl)benzaldehydeHCID 70353925HCID 70353925, compound

Product 1

HCID 704356234-(2-Benzylmercaptophenyl)-1,4-dihydro-2,6-dimethyl-5-nitropyridine-3-carboxylic acid N-[4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10 mmoles of 2-benzylmercaptobenzaldehyde, 15 mmoles of nitroacetone and 10 mmoles of 3-aminocrotonic acid N-[4-(6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)-phenyl]-amide in 30 ml of isopropanol are heated at 60°-70° C. for 10 hours. The reaction mixture is concentrated and the residue is taken up in chloroform and chromatographed over silica gel using chloroform to which methanol is added. The product is recrystallized from isopropanol.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customchromatographed over silica gel
  3. additionis added
  4. customThe product is recrystallized from isopropanol

Sources & evidence

ORD record
ord-2f217b0ecf554432a8b63ae406eeb837
Source dataset
uspto-grants-1987_11
Patent number
US04707479

Reaction notes

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