Hydrochloric Acid → HCID 13371118, compound

HRID 1154360Notes

Reaction equation

HRID 1154360 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[K+].C(O)C.Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[C:12]2[CH:22]=[CH:21][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 86120870HCID 86120870, compound

Product 1

HCID 13371118HCID 13371118, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.6 g. of 4-[bis[3-(p-chlorophenyl)propyl]amino]benzoic acid, ethyl ester and 3 g. of 85% potassium hydroxide in 50 ml. of ethanol is stirred at 75° C. for 4 hours, cooled, diluted with 100 ml. of water, and adjusted to pH 6.0 with 37% hydrochloric acid. The solution is extracted with two 150 ml. portions of ether. The ether extracts are combined, washed with 100 ml. of water, then 100 ml. of brine, dried over magnesium sulfate, and evaporated to an orange solid. This solid is recrystallized twice from 50 ml. of acetonitrile, giving 1.39 g. of the desired product, m.p. 128°-131° C.

Workup

  1. temperaturecooled
  2. additiondiluted with 100 ml
  3. extractionThe solution is extracted with two 150 ml
  4. washwashed with 100 ml
  5. dry with materialof brine, dried over magnesium sulfate
  6. customevaporated to an orange solid
  7. customThis solid is recrystallized twice from 50 ml
  8. customof acetonitrile, giving 1.39 g

Sources & evidence

ORD record
ord-5016750225a645af9a14218fde99f01c
Source dataset
uspto-grants-1984_12
Patent number
US04489094

Reaction notes

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