Nitrogen → N,N-Dimethyl-2-[N-(3-hydroxypropyl)-N-methylaminosulfonyl]-6-nitrobenzamide

HRID 2309214Notes

Reaction equation

HRID 2309214 reaction equation
[CH3:1][N:2]([CH3:22])[C:3](=[O:21])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[S:13]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])(=[O:15])=[O:14].[H-].[Na+].N#N.[H][H].[CH3:29]C1C=CC(S(C)(=O)=O)=CC=1>CN(C=O)C.C(OCC)(=O)C>[CH3:22][N:2]([CH3:1])[C:3](=[O:21])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[S:13]([N:16]([CH2:17][CH2:18][CH2:19][OH:20])[CH3:29])(=[O:15])=[O:14]

Participants

8

Reactant 5

HCID 947NitrogenHCID 18521p-Tolyl methyl sulfoneHCID 24758Sodium hydrideHCID 13881299HCID 13881299, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20186096N,N-Dimethyl-2-[N-(3-hydroxypropyl)-N-methylaminosulfonyl]-6-nitrobenzamideYield 116.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

N,N-Dimethyl-2-[N-(3-hydroxypropyl)aminosulfonyl]-6-nitrobenzamide (1.37 g, 4.13 mmol) in 12 ml of DMF, was added dropwise to a suspension of 198 mg (4.13 mmol) of 50% NaH in 3 ml of DMF in an atmosphere of N2. When evolution of hydrogen was complete, a solution of methyl p-toluene sulfonate (0.794 g, 4.14 mmol) in DMF, 2 ml, was added. The clear deep Yellow solution was stirred at 25° for 17 hours, then at 60° for 23 hours. The solution then was mixed with 175 ml of ethyl acetate and the precipitate that separated collected on a filter and washed with 50 ml of ethyl acetate. The combined filtrate and washings were extracted with 6×25 ml of saturated NaCl solution and the ethyl acetate evaporated to give 1.66 g of a clear yellow oil. Flash chromatography over E. Merck silica gel 60 (230-400 mesh) gave 0.49 g of a clear light yellow oil. This material was dissolved in 50 ml of CHCl3, the solution extracted with 4×5 ml of lN NaOH, then with 3 x 5 ml of saturated NaCl and dried over MgSO4.After evaporation of the CHCl3, the residue was dissolved in ethyl acetate and the solution filtered to remove a trace of MgSO4. Evaporation of the solvent gave 0.44 g of light yellow crystalline product, m.p., 91.5°-92.5°.

Workup

  1. waitat 60° for 23 hours
  2. customthe precipitate that separated
  3. customcollected on
  4. filtrationa filter
  5. washwashed with 50 ml of ethyl acetate
  6. extractionThe combined filtrate and washings were extracted with 6×25 ml of saturated NaCl solution
  7. customthe ethyl acetate evaporated

Sources & evidence

ORD record
ord-7157e8b89e93439ea341afef532c9c81
Source dataset
uspto-grants-1987_09
Patent number
US04694020

Reaction notes

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