Water → HCID 14423207, compound

HRID 893832Notes

Reaction equation

HRID 893832 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH2:14][CH2:13][CH2:12][C:11]=1[N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:9].N[C:21]1C=CC=C[CH:22]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH2:14][CH2:13][CH2:12][C:11]=1[NH:15][C:19]1[CH:18]=[CH:17][CH:16]=[CH:22][CH:21]=1)=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 15135970HCID 15135970, compound

Product 1

HCID 14423207HCID 14423207, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Reflux a solution of (2-bromophenyl)[2-(1-pyrrolidinyl)-1-cyclopenten-1-yl]-methanone (14.1 g) (from Preparative Example 1) in benzene (100 ml) containing aniline (4.5 ml) and p-toluenesulfonic acid monohydrate (8.8 g) for 19 hrs. Remove water continuously with a Dean-Stark trap. Wash the cooled solution with water, 1M NaHCO3 solution, and with water. Dry the benzene solution, filter it, and evaporate the solvent. Crystallize to obtain (2-bromophenyl)[2-(phenylamino)-1-cyclopenten-1-yl]-methanone, m.p. 106-5°-108.5° from CH3CN.

Workup

  1. washWash the cooled solution with water, 1M NaHCO3 solution
  2. dry with materialDry the benzene solution
  3. filtrationfilter it
  4. customevaporate the solvent
  5. customCrystallize

Sources & evidence

ORD record
ord-25a876e50d0a468dab44fc6ef6f4a0d5
Source dataset
uspto-grants-1992_06
Patent number
US05126352

Reaction notes

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