Hydrochloric Acid → N-(2-methoxy-5-nitrophenyl)methanesulfonamide

HRID 19974

Reaction equation

HRID 19974 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5].[CH3:13][S:14](Cl)(=[O:16])=[O:15].Cl>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH:5][S:14]([CH3:13])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74472-Methoxy-5-nitroanilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 743556N-(2-methoxy-5-nitrophenyl)methanesulfonamideYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a solution of 2-methoxy-5-nitroaniline (5 g) in pyridine (25 ml) at 0° C. was added dropwise methanesulfonyl chloride (3.5 ml) then pyridine (0.5 ml). The mixture was left at 0° C. for 1 hour, then brought to RT for 2 h. The mixture was poured onto ice (100 g) and dilute hydrochloric acid (3M, 100 ml), the solid formed was filtered then washed with water to give 2-Methoxy-5-nitro-methanesulfonylaminobenzene (5.2 g, 71%) as an off-white crystalline solid.

Workup

  1. waitbrought to RT for 2 h
  2. customthe solid formed
  3. filtrationwas filtered
  4. washthen washed with water

Sources & evidence

ORD record
ord-8d5029afaa1540ef99f15031c5792ee7
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Linked notes

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