Benzoic acid, 2-chloro-5-(chlorosulfonyl)- → HCID 20505864, compound

HRID 355121Notes

Reaction equation

HRID 355121 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH2:24])=[CH:18][CH:17]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([NH:24][CH2:23][CH2:22][C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 67306Benzoic acid, 2-chloro-5-(chlorosulfonyl)-HCID 674302-(4-Chlorophenyl)ethylamine

Product 1

HCID 20505864HCID 20505864, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-chlorosulfonyl benzoic acid, 3.5 g. (0.014 mole), is added to a solution of 2-(p-chlorophenyl)ethylamine, 6.5 g. (0.042 mole) in 25 ml. methylene chloride. The resulting slurry is stirred overnight and filtered to recover 9.7 g. of residue. This is recrystallized three times from aqueous isopropanol, then dissolved in 1 N aqueous sodium hydroxide, washed three times with ether, and then acidified with conc. hydrochloric acid. The resulting precipitate is recrystallized twice from aqueous isopropanol to yield the desired product, m.p. 176°-178° C.

Workup

  1. filtrationfiltered
  2. customto recover 9.7 g
  3. customThis is recrystallized three times from aqueous isopropanol
  4. dissolutiondissolved in 1 N aqueous sodium hydroxide
  5. washwashed three times with ether
  6. customThe resulting precipitate is recrystallized twice from aqueous isopropanol

Sources & evidence

ORD record
ord-ae750f8829a0456dbba0ef8f8bf428a7
Source dataset
uspto-grants-1983_03
Patent number
US04377521

Reaction notes

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