Water → HCID 3030030, compound

HRID 1510194Notes

Reaction equation

HRID 1510194 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 N2SO4. 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. customThe combined organic phase was dried over N2SO4
  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-f3e682818cbe4953946439e83f768150
Source dataset
uspto-grants-2012_07
Patent number
US08211916B2

Reaction notes

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