Hydrochloric Acid → 4-(11-Mercaptoundecylamino)benzoic acid

HRID 1106170Notes

Reaction equation

HRID 1106170 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=1.NC(N)=[S:27].[OH-].[Na+].Cl>C(O)C>[SH:27][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 20482498Ethyl 4-(11-bromoundecylamino)benzoate

Product 1

HCID 204825874-(11-Mercaptoundecylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10 g. of ethyl 4-[(11-bromoundecyl)amino]benzoate and 2.0 g. of thiourea in 80% of 95% ethanol is stirred under reflux for 3 hours, allowed to cool, treated with 12 ml. of 10 N aqueous sodium hydroxide solution and again stirred under reflux for 2 hours. The mixture is acidified with dilute hydrochloric acid and filtered. The solid is recrystallized from ethanol-water to yield the product as a white solid.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureto cool
  3. additiontreated with 12 ml
  4. temperatureunder reflux for 2 hours
  5. filtrationfiltered
  6. customThe solid is recrystallized from ethanol-water

Sources & evidence

ORD record
ord-29bffda4f743419f8b69f1d8919667f7
Source dataset
uspto-grants-1982_01
Patent number
US04311846

Reaction notes

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