Methylamine → 5-Methylsulphamyl-3-nitro-4-phenoxy-benzoic acid

HRID 918601Notes

Reaction equation

HRID 918601 reaction equation
[CH3:1][NH2:2].Cl[C:4]1[C:12]([S:13](Cl)(=[O:15])=[O:14])=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[N+:17]([O-:19])=[O:18].[OH-:20].[Na+]>>[CH3:1][NH:2][S:13]([C:12]1[C:4]([O:20][C:4]2[CH:12]=[CH:11][CH:7]=[CH:6][CH:5]=2)=[C:5]([N+:17]([O-:19])=[O:18])[CH:6]=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])(=[O:15])=[O:14]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 898924-Chloro-5-chlorosulfonyl-3-nitrobenzoic acid

Product 1

HCID 215060385-Methylsulphamyl-3-nitro-4-phenoxy-benzoic acid

Procedure

To a mixture of 1N sodium hydroxide (60 ml) and aqueous methylamine (3.43 g containing 1.2 g of methylamine) 4-chloro-5-chlorosulphonyl-3-nitro-benzoic acid (9.3 g) was added in portions, while stirring and keeping the mixture at 0°-3°C. Then the reaction mixture was left standing until it reached room temperature, after which the 4-chloro-5-methylsulphamyl-3-nitro-benzoic acid was precipitated by slow acidification with 4N hydrochloric acid. The precipitate was collected by suction and recrystallized from aqueous ethanol. The melting point was 228°-229°C.

Workup

  1. additionwas added in portions
  2. customat 0°-3°C
  3. waitThen the reaction mixture was left
  4. customreached room temperature
  5. customafter which the 4-chloro-5-methylsulphamyl-3-nitro-benzoic acid was precipitated by slow acidification with 4N hydrochloric acid
  6. customThe precipitate was collected by suction
  7. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-59c5dee16efb4cbab541b08714bd866d
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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