Triethylamine → N-methoxy-4,N-dimethyl-3-sulfamoyl-benzamide

HRID 1515482Notes

Reaction equation

HRID 1515482 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].Cl.[CH3:16][NH:17][O:18][CH3:19].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[CH3:19][O:18][N:17]([CH3:16])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([S:11](=[O:14])(=[O:13])[NH2:12])[CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2395854-Methyl-3-sulfamoylbenzoic acid

Product 1

HCID 86649834N-methoxy-4,N-dimethyl-3-sulfamoyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.63 g of 4-methyl-3-sulfamoyl-benzoic acid, 1.92 g of N,O-dimethylhydroxylamine hydrochloride, and 5.02 mL of triethylamine in methylene chloride (120 mL) is treated with 8.32 g of benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate. The reaction mixture is stirred overnight at room temperature, washed sequentially with saturated aqueous sodium bicarbonate, water and a saturated sodium chloride solution, dried (magnesium sulfate) and concentrated in vacuo. The crude material is purified by silica gel chromatography (1:2 hexanes/ethyl acetate) to give N-methoxy-4,N-dimethyl-3-sulfamoyl-benzamide as a white powder. MS (m/z): 257 (M−1); Rf 0.25 (1:2 hexanes/ethyl acetate).

Workup

  1. washwashed sequentially with saturated aqueous sodium bicarbonate, water
  2. dry with materiala saturated sodium chloride solution, dried (magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customThe crude material is purified by silica gel chromatography (1:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-9107e4473a924a5aad1181489cd5023f
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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