Hydrochloric Acid → HCID 45381534, compound

HRID 1402835Notes

Reaction equation

HRID 1402835 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:24])[CH2:11][CH:12]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH2:13][C:14]([OH:16])=[O:15].Cl>C(OCC)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[O:24][C:10]([CH2:11][CH:12]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[CH2:13][C:14]([OH:16])=[O:15])=[N:9][C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66759860HCID 66759860, compound

Product 1

HCID 45381534HCID 45381534, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Neat N-(2-hydroxy-5-chlorophenyl)-3-(4-chlorophenyl)glutaramic acid (1.5 g) was kept under vacuum (membrane pump) and placed in a preheated (230° C.) oil bath. The resulting melt was stirred at this temperature under vacuum for 1 h. The melt was cooled and close to the point of solidification diethyl ether was added to give a cloudy solution. The traces of solid were removed by filtration and the filtrate was shaken with 20% NaOH solution (20 ml). The sodium salt of the product separates as ether and water insoluble brownish oil. The neat oil is isolated and treated with 10% HCl (2 ml). The desired product separates as slowly solidifying oil which is triturated with methanol/water 1:2 and with acetone to afford 0.16 g of 4-(5-chloro-2-benzoxazolyl)-3-(4-chlorophenyl)butanoic acid as almost colourless solid.

Workup

  1. customplaced in a preheated (230° C.) oil bath
  2. temperatureThe melt was cooled
  3. additionwas added
  4. customto give a cloudy solution
  5. customThe traces of solid were removed by filtration
  6. stirringthe filtrate was shaken with 20% NaOH solution (20 ml)
  7. customThe neat oil is isolated
  8. customThe desired product separates as slowly solidifying oil which is triturated with methanol/water 1:2 and with acetone

Sources & evidence

ORD record
ord-a32be7215711462e930213e83ffcd6bc
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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