Hydrochloric Acid → HCID 11708770, compound

HRID 1768129Notes

Reaction equation

HRID 1768129 reaction equation
[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1(=O)[O:20][CH2:19][CH2:18][CH2:17]1.Cl>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:13]2[CH2:16][CH2:17][CH2:18][C:19]2=[O:20])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7302Gamma-ButyrolactoneHCID 228604-Benzyloxyaniline

Product 1

HCID 11708770HCID 11708770, compoundYield 31%

Procedure

20.3 g (101.9 mmol) 4-benzyloxyaniline and 9.1 ml (119.2 mmol) gamma-butyro-lactone are treated with 3 ml concentrated hydrochloric acid. The mixture is heated 20 hours to 160° C., then 5.5 hours to 200° C. After cooling, the mixture is extracted with 250 ml ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate and dried. Evaporation of the solvent and recrystallisation from diethyl ether yields 8.4 g (31%) of a brownish solid. MS: m/e=267 (M+).

Workup

  1. temperatureThe mixture is heated 20 hours to 160° C.
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with 250 ml ethyl acetate
  4. washwashed with saturated aqueous sodium hydrogencarbonate
  5. customdried
  6. customEvaporation of the solvent and recrystallisation from diethyl ether

Sources & evidence

ORD record
ord-0f1faad2cbec45739012e4a6c92ada6f
Source dataset
uspto-grants-2007_06
Patent number
US07235581B2

Reaction notes

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