Methane → N-methyl-N-(phenylmethoxy)-2-aminobenzenesulfonamide

HRID 1105759Notes

Reaction equation

HRID 1105759 reaction equation
[CH3:1][N:2]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O)(=[O:5])=[O:4].O.C>C(O)(=O)C.[Fe]>[CH3:1][N:2]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:12])(=[O:4])=[O:5]

Participants

6

Reactant 3

HCID 297MethaneHCID 962WaterHCID 20478825N-methyl-N-(phenylmethoxy)-2-nitrobenzenesulfonamide

Product 1

HCID 20478836N-methyl-N-(phenylmethoxy)-2-aminobenzenesulfonamideYield 36.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 88.9 g of the product of Example 33 in 565 ml of 90% aqueous acetic acid was added 83 g of iron powder at 80°-90° in several portions. Water (60 ml) was then added and heating continued for 20 minutes. Charcoal (10 g) was added and the solution filtered through Celite® and concentrated in-vacuo. The residue was made strongly alkaline with 20% NaOH solution, then extracted with methylene chloride. The extract was dried and concentrated in-vacuo to give 29.3 g of N-methyl-N-(phenylmethoxy)-2-aminobenzenesulfonamide as a yellow oil. [NMR:δ5.1(broad singlet, 2H, NH2)].

Workup

  1. temperatureheating
  2. filtrationthe solution filtered through Celite®
  3. concentrationconcentrated in-vacuo
  4. extractionextracted with methylene chloride
  5. customThe extract was dried
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-823a26ddfdd047ca9ca60da1c0b2b877
Source dataset
uspto-grants-1982_01
Patent number
US04310346

Reaction notes

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