Methyl 4-chloro-3-[[[(dimethylamino)methylene]amino]sulfonyl]-5-nitrobenzoate → HCID 54331231, compound

HRID 2412432Notes

Reaction equation

HRID 2412432 reaction equation
Cl[C:2]1[C:11]([S:12]([N:15]=[CH:16][N:17]([CH3:19])[CH3:18])(=[O:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].[OH:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.[K]>CN(C)C=O>[CH3:18][N:17]([CH:16]=[N:15][S:12]([C:11]1[C:2]([O:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[C:3]([N+:20]([O-:22])=[O:21])[CH:4]=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:14])=[O:13])[CH3:19]

Participants

4

Reactant 2

HCID 53736204Methyl 4-chloro-3-[[[(dimethylamino)methylene]amino]sulfonyl]-5-nitrobenzoateHCID 66797238HCID 66797238, compound

Product 1

HCID 54331231HCID 54331231, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 200 g (0.57 mole) of methyl 4-chloro-5-dimethylaminomethyleneaminosulfonyl-3-nitro-benzoate and 93 g (0.7 mole) of potassium 3-hydroxypyridine in 1 l of dimethylformamide is stirred for 1.5 hours at 80° C. and, after cooling, is introduced into 4-5 l of ice-water, while stirring vigorously. The product which has precipitated is filtered off, washed with H2O and recrystallized from dimethylformamide/CH3OH.

Workup

  1. temperatureafter cooling
  2. customThe product which has precipitated
  3. filtrationis filtered off
  4. washwashed with H2O
  5. customrecrystallized from dimethylformamide/CH3OH

Sources & evidence

ORD record
ord-2d2e6d407c1f4ebcb726643b64c6d9d9
Source dataset
uspto-grants-1985_01
Patent number
US04492710

Reaction notes

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