3-Chlorophenol → 4-(m-Chlorophenoxy)-3-nitro-5-sulphamyl-benzoic acid

HRID 918608Notes

Reaction equation

HRID 918608 reaction equation
Cl[C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[Cl:18][C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1.C(=O)(O)[O-].[Na+]>O>[Cl:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[O:25][C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 215060844-(m-Chlorophenoxy)-3-nitro-5-sulphamyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-chloro-3-nitro-5-sulphamyl-benzoic acid (28 g), m-chlorophenol (26 g), sodium bicarbonate (34 g), and water (200 ml) was stirred at 85°C for 10 hours. After cooling, excess m-chlorophenol was removed by extraction with diethyl ether, and 4-(m-chlorophenoxy)-3-nitro-5-sulphamyl-benzoic acid was precipitated from the aqueous layer by the addition of 4N hydrochloric acid. After recrystallization from aqueous methanol, the melting point was 230°-232°C.

Workup

  1. temperatureAfter cooling
  2. customexcess m-chlorophenol was removed by extraction with diethyl ether, and 4-(m-chlorophenoxy)-3-nitro-5-sulphamyl-benzoic acid
  3. customwas precipitated from the aqueous layer by the addition of 4N hydrochloric acid
  4. customAfter recrystallization from aqueous methanol

Sources & evidence

ORD record
ord-45f881ade9bd44aab588515e535601a0
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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