3-Bromo-4-(4-chlorophenyl)-4-oxobutanoic acid → Hydrogen Bromide

HRID 543882Notes

Reaction equation

HRID 543882 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH2:6][N:7]1[CH2:12][NH:11][C:10](=[S:13])[NH:9][CH2:8]1.[Br:17][CH:18]([C:23](=O)[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[CH2:19][C:20]([OH:22])=[O:21].N1C=CC(=S)NN=1>CO>[C:20]([CH2:19][C:18]1[S:13][C:10]2=[N:11][CH2:12][N:7]([CH2:6][C:5]3[CH:14]=[CH:15][CH:16]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:8][N:9]2[C:23]=1[C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1)([OH:22])=[O:21].[BrH:17]

Participants

6

Reactant 3

HCID 1696663-Bromo-4-(4-chlorophenyl)-4-oxobutanoic acidHCID 21226029HCID 21226029, compoundHCID 86739400HCID 86739400, compound

Product 2

HCID 260Hydrogen BromideYield 296.6%HCID 13059235HCID 13059235, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(m-Methoxybenzyl)-3,4,5,6-tetrahydro-s-triazin-2(1H) thione (2.37 g, 0.01 mole) was partly dissolved in methanol (100 ml) at 45° C. and 3-bromo-3-(p-chlorobenzoyl) propionic acid (2.92 g, 0.01 mole) dissolved in the same solvent (50 ml) was added. The temperature was held at about 45° C. until all the triazinthione dissolved, and the mixture was then allowed to stand for 3 hours. The solvent was evaporated to give a pale yellow foam, which was triturated with isopropanol to give the title compound hydrobromide hemipropanolate (2.4 g, 44%) m.p. 123°-125° C.

Workup

  1. additionwas added
  2. customwas held at about 45° C. until all
  3. dissolutiondissolved
  4. customThe solvent was evaporated
  5. customto give a pale yellow foam, which
  6. customwas triturated with isopropanol

Sources & evidence

ORD record
ord-d72a8f5ee7b24645a55c952948c7aab1
Source dataset
uspto-grants-1984_05
Patent number
US04447604

Reaction notes

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