Isopropylamine → 4-Isopropylamino-3-nitro-5-sulphamyl-benzoic acid

HRID 1287742Notes

Reaction equation

HRID 1287742 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Cl[C:6]1[C:14]([S:15](=[O:18])(=[O:17])[NH2:16])=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[N+:19]([O-:21])=[O:20]>O>[CH:1]([NH:4][C:6]1[C:14]([S:15](=[O:17])(=[O:18])[NH2:16])=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[N+:19]([O-:21])=[O:20])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 215060114-Isopropylamino-3-nitro-5-sulphamyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Isopropylamine (120 ml) and water 8 ml) were added to 4-chloro-3-nitro-5-sulphamyl-benzoic acid (22.4 g), while cooling. Then the reaction mixture was stirred for 5 days at room temperature. After evaporation in vacuo, the residue was triturated with 4N hydrochloric acid, after which the resulting 4-isopropylamino-3-nitro-5-sulphamyl-benzoic acid was collected by suction. After recrystallization from aqueous ethanol, the acid was obtained with a melting point of 206°C (decomp.).

Workup

  1. temperaturewhile cooling
  2. customAfter evaporation in vacuo
  3. customthe residue was triturated with 4N hydrochloric acid
  4. customafter which the resulting 4-isopropylamino-3-nitro-5-sulphamyl-benzoic acid was collected by suction
  5. customAfter recrystallization from aqueous ethanol
  6. customthe acid was obtained with a melting point of 206°C (decomp.)

Sources & evidence

ORD record
ord-1c5b5898335d45e69928dec77b6d82cc
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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