4-Methoxy-2-nitroaniline → 2-(4-(4-Methoxy-2-nitrophenylaminosulfonyl)phenoxy)acetamide

HRID 1593262Notes

Reaction equation

HRID 1593262 reaction equation
Cl[S:2]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([NH2:13])=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:16][O:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[C:20]([N+:25]([O-:27])=[O:26])[CH:19]=1>N1C=CC=CC=1>[CH3:16][O:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][S:2]([C:5]2[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([NH2:13])=[O:12])=[CH:7][CH:6]=2)(=[O:4])=[O:3])=[C:20]([N+:25]([O-:27])=[O:26])[CH:19]=1

Participants

4

Reactant 2

HCID 667934-Methoxy-2-nitroanilineHCID 116444964-(2-Amino-2-oxoethoxy)benzenesulfonyl chloride

Product 1

HCID 117178662-(4-(4-Methoxy-2-nitrophenylaminosulfonyl)phenoxy)acetamideYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Solid 2-[4-(chlorosulfonyl)phenoxy]acetamide (Intermediate A91, 65.87 g, 0.264 mol) was added to a solution of 4-methoxy-2-nitroaniline (27.72 g, 0.165 mol) in pyridine (500 mL) at room temperature under argon. The resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. To the residue was added 0.5 M hydrochloric acid (1000 mL) and stirred for 30 min. The orange solid was collected and recrystallized from acetone to give 42.8 g (68%) of the title compound, nitro sulfonamide as yellow crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added 0.5 M hydrochloric acid (1000 mL)
  3. stirringstirred for 30 min
  4. customThe orange solid was collected
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-2c5c5e722d2d4a8a989ae8a9272059c2
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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