Hydrochloric Acid → 4-(4-hydroxyphenylthiomethyl)-N-phenylbenzamide

HRID 1375334Notes

Reaction equation

HRID 1375334 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[K+].Cl[CH2:12][C:13]1[CH:27]=[CH:26][C:16]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])=[CH:15][CH:14]=1.Cl>O.CO>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])=[CH:26][CH:27]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide2×HCID 2401474-MercaptophenolHCID 114139054-(chloromethyl)-N-phenylbenzamide

Product 1

HCID 114049084-(4-hydroxyphenylthiomethyl)-N-phenylbenzamideYield 84.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

In a 200 ml four-necked flask equipped with a stirrer and a thermometer, 1.34 g (10.6 mmol) of 4-mercaptophenol, 0.7 g (10.6 mmol) of potassium hydroxide and 50 ml of methanol were added at room temperature. After confirming that potassium hydroxide has been dissolved, the inner temperature was cooled to 10° C. and 2.6 g (10.6 mmol) of 4-chloromethyl-N-phenylbenzamide was added, followed by stirring at room temperature for 3 hours. After the completion of the reaction, the reaction solution was acidified with hydrochloric acid and 50 ml of water was added, and then the deposited crystal was collected by filtration to obtain 3.0 g of 4-(4-hydroxyphenylthiomethyl)-N-phenylbenzamide. The yield was 84%. The melting point was 220–222° C.

Workup

  1. customIn a 200 ml four-necked flask equipped with a stirrer
  2. dissolutionhas been dissolved
  3. customAfter the completion of the reaction
  4. additionwas added
  5. filtrationthe deposited crystal was collected by filtration

Sources & evidence

ORD record
ord-812d217a9aed443fae903151b2593521
Source dataset
uspto-grants-2007_01
Patent number
US07169737B2

Reaction notes

Loading…