m-Chloroperbenzoic acid → HCID 13094329, compound

HRID 464188Notes

Reaction equation

HRID 464188 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[CH2:7][CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1.ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[CH2:7][CH2:8][N+:9]([O-:29])=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12948279HCID 12948279, compound

Product 1

HCID 13094329HCID 13094329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6.4 g (22 mmole) of 8-chloro-1-(2-fluorophenyl)-3,4-dihydro-5H-2-benzazepin-5-one and 6.4 g (34 mmole) of m-chloroperbenzoic acid in 350 ml of methylene chloride was stirred at room temperature for 2 hr. The methylene chloride solution was washed with saturated aqueous sodium bicarbonate and water, dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a yellow oil. The oil was crystallized from a mixture of ether and petroleum ether to give off-white prisms, mp 166°-168° C. Recrystallization from a mixture of ether and methylene chloride gave colorless prisms, mp 168°-170° C.

Workup

  1. washThe methylene chloride solution was washed with saturated aqueous sodium bicarbonate and water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure
  4. customto give a yellow oil
  5. customThe oil was crystallized from a mixture of ether and petroleum ether
  6. customto give off-white prisms, mp 166°-168° C
  7. customRecrystallization
  8. additionfrom a mixture of ether and methylene chloride
  9. customgave colorless prisms, mp 168°-170° C.

Sources & evidence

ORD record
ord-894782d4e3214baa84901b9a218c1a8e
Source dataset
uspto-grants-1985_10
Patent number
US04546183

Reaction notes

Loading…