3-Bromo-4-(4-chlorophenyl)-4-oxobutanoic acid → 4-hydroxyfentiazac

HRID 851473Notes

Reaction equation

HRID 851473 reaction equation
Br[CH:2]([C:7](=O)[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH2:3][C:4]([OH:6])=[O:5].[OH:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH2:23])=[S:22])=[CH:19][CH:18]=1>CN(C)C=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[N:23]=[C:21]([C:20]3[CH:24]=[CH:25][C:17]([OH:16])=[CH:18][CH:19]=3)[S:22][C:2]=2[CH2:3][C:4]([OH:6])=[O:5])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 1696663-Bromo-4-(4-chlorophenyl)-4-oxobutanoic acidHCID 27593444-Hydroxythiobenzamide

Product 1

HCID 1289074-hydroxyfentiazacYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromo-3-(4-chlorobenzoyl)propionic acid (27 g), and 4-hydroxy-thiobenzamide (14.6 g) were heated to 80° in dimethylformamide (50 ml). The reactants were kept at this temperature for 1 hour, cooled and poured onto ice. The resulting gum solidified, and was filtered, and washed with water, to give 31.6 g of powder, m.p. 184°-194° C. (decomp.). This was recrystallised from aqueous isopropanol affording 25.4 g of the title compound, hemihydrate, m.p. 192°-194° (d).

Workup

  1. temperaturecooled
  2. additionpoured onto ice
  3. filtrationwas filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-c04537fd1a774cf4abc6374af5f60334
Source dataset
uspto-grants-1983_05
Patent number
US04385059

Reaction notes

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