Hydrochloric Acid → N-benzyl-3-(2-hydroxyethyl)-2-biphenylcarboxamide

HRID 27245Notes

Reaction equation

HRID 27245 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:17]=2[C:15](=[O:16])[O:14][CH2:13][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N)C1C=CC=CC=1.Cl>>[CH2:19]([NH:26][C:15]([C:17]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][CH:9]=[CH:10][C:11]=1[CH2:12][CH2:13][OH:14])=[O:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 129985681-Phenylmethanamine--hydrogen bromide (1/1)HCID 233443663,4-Dihydro-8-phenylisocoumarin

Product 1

HCID 23344336N-benzyl-3-(2-hydroxyethyl)-2-biphenylcarboxamide

Conditions

Temperature
160 °C

Procedure

A mixture of 7.84 parts of 3,4-dihydro-8-phenylisocoumarin and 8 parts of benzylamine hydrobromide in 40 parts by volume of benzylamine is stirred at about 160° C. for about 4 hours. The reaction solution is then cooled and poured into 500 parts by volume of 5% hydrochloric acid. The oil which separates is extracted into methylene chloride and the extracts are washed with several portions of 5% hydrochloric acid, water, dried over anhydrous magnesium sulfate and the solvent removed to give, as a solid, N-benzyl-3-(2-hydroxyethyl)-2-biphenylcarboxamide. The solid is recrystallized from a mixture of chloroform and hexane to give white flocculant crystals melting at about 129°-130° C. This compound has the following formula ##STR13##

Workup

  1. temperatureThe reaction solution is then cooled
  2. extractionThe oil which separates is extracted into methylene chloride
  3. washthe extracts are washed with several portions of 5% hydrochloric acid, water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent removed

Sources & evidence

ORD record
ord-f18e2c3b068e4388813cd516dedeb43d
Source dataset
uspto-grants-1980_09
Patent number
US04220778

Reaction notes

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