Hydrogen Bromide → HCID 54275757, compound

HRID 1112512Notes

Reaction equation

HRID 1112512 reaction equation
C(OC([CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([C:19]1[NH:20][C:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:22]2[C:27]=1[CH:26]=[CH:25][C:24]([Cl:28])=[CH:23]2)=[O:18])=O)C1C=CC=CC=1.Br.C(OCC)C>C(O)(=O)C>[CH3:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([C:19]1[NH:20][C:21]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[C:22]2[C:27]=1[CH:26]=[CH:25][C:24]([Cl:28])=[CH:23]2)=[O:18]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 86736120HCID 86736120, compound

Product 1

HCID 54275757HCID 54275757, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

9.5 G. of 5-chloro-3-phenylisoindole-1-carboxylic acid {3-[(benzyloxycarbonyl)methylamino]propyl}amide are dissolved in 20 ml. of glacial acetic acid and 30 ml. of a solution of 33% hydrobromic acid in glacial acetic acid are added thereto. The mixture is allowed to stand at room temperature for 2 hours with occasional agitation and it is thereafter poured into 300 ml. of diethyl ether. The separated hydrobromide is removed by filtration under suction, washed with diethyl ether and treated with 200 ml. of 2-N ammonium hydroxide solution. The liberated base is extracted with methylene chloride and the extract washed with water, dried over sodium sulfate and evaporated to dryness. After crystallization of the solid residue from ethanol, there is obtained 5-chloro-3-phenylisoindole-1-carboxylic acid [3-(methylamino)propyl]amide in the form of yellowish crystals having a melting point of 162°-164° C.

Workup

  1. additionis thereafter poured into 300 ml
  2. customThe separated hydrobromide is removed by filtration under suction
  3. washwashed with diethyl ether
  4. additiontreated with 200 ml
  5. extractionThe liberated base is extracted with methylene chloride
  6. washthe extract washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness
  9. customAfter crystallization of the solid residue from ethanol

Sources & evidence

ORD record
ord-19b5611dad9749b7bf180ec210423eee
Source dataset
uspto-grants-1978_10
Patent number
US04122265

Reaction notes

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