Water → HCID 3030030, compound

HRID 890351Notes

Reaction equation

HRID 890351 reaction equation
Cl[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].CCN(CC)CC.O>CN(C=O)C>[CH:2]([O:15][N:16]1[C:17](=[O:26])[C:18]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]2[C:20]1=[O:21])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7035ChlorodiphenylmethaneHCID 8471TriethylamineHCID 10665N-Hydroxyphthalimide

Product 1

HCID 3030030HCID 3030030, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-chloro-1,1-diphenylmethane (3.42 g, 16.93 mmol), N-hydroxyphthalimide (2.30 g, 14.11 mmol) and Et3N (3.0 ml) in DMF (50 ml) was stirred at 60° C. under N2 for 8 hours. After the reaction mixture was cooled to room temperature, water (100 ml) was added. The mixture was extracted with Et2O. The combined organic phase was dried over Na2SO4. After evaporation of the solvent, the crude product was purified by chromatography(Hexane/Benzene/EtOAc=20/10/3) to give a white solid, 3.95 g (85% yield). 1H NMR (CD3Cl) δ 7.72-7.63 (1H, m), 7.56-7.53 (1H, m), 7.40-7.24 (12H, m), 5.85 (1H, s, Ph2CH).

Workup

  1. extractionThe mixture was extracted with Et2O
  2. dry with materialThe combined organic phase was dried over Na2SO4
  3. customAfter evaporation of the solvent
  4. customthe crude product was purified by chromatography(Hexane/Benzene/EtOAc=20/10/3)
  5. customto give a white solid, 3.95 g (85% yield)

Sources & evidence

ORD record
ord-4de9843a971a4a58bda057f771fbe731
Source dataset
uspto-grants-2006_02
Patent number
US06995268B2

Reaction notes

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