Hydrochloric Acid → HCID 14049970, compound

HRID 580544Notes

Reaction equation

HRID 580544 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][N:8]2C(=O)C3=CC=CC=C3C2=O)=[CH:4][C:3]=1[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N)CCC.[ClH:33]>C(O)C>[ClH:33].[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][NH2:8])=[CH:4][C:3]=1[O:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8007ButylamineHCID 14049968HCID 14049968, compound

Product 1

HCID 14049970HCID 14049970, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-fluoro-3-phenoxybenzyloxy)phthalimide 5 g, 14 mmol), n-butylamine (1.13 g, 15 mmol) and absolute ethanol (3 ml) were placed in a dry flask under a nitrogen atmosphere. This reaction mixture was stirred at 60°-75° for 1.5 hours, cooled and adjusted to pH 3 using dry hydrogen chloride gas. The solution was concentrated to 10 ml and poured into dry ether. The resulting white precipitate was filtered off and recrystallized from petroleum spirit (40°-60°)/dichloromethane to give 3.2 g (87%) of a white solid, m.p. 149.3°.

Workup

  1. temperaturecooled
  2. concentrationThe solution was concentrated to 10 ml
  3. additionpoured into dry ether
  4. filtrationThe resulting white precipitate was filtered off
  5. customrecrystallized from petroleum spirit (40°-60°)/dichloromethane

Sources & evidence

ORD record
ord-792234ca64b040ee960ab96f40c2edf5
Source dataset
uspto-grants-1988_06
Patent number
US04753960

Reaction notes

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