Chloroacetyl chloride → HCID 21480476, compound

HRID 1490109Notes

Reaction equation

HRID 1490109 reaction equation
[C:1]([NH:5][C:6]1[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])([CH3:4])([CH3:3])[CH3:2].[Cl:20][CH2:21][C:22](Cl)=[O:23]>C1(C)C=CC=CC=1>[Cl:20][CH2:21][C:22]([N:5]([C:6]1[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=1[C:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:9])[C:1]([CH3:4])([CH3:2])[CH3:3])=[O:23]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 21480479HCID 21480479, compound

Product 1

HCID 21480476HCID 21480476, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(tert-butylamino)benzophenone (7.5 g) and chloroacetyl chloride (20 ml) in anhydrous toluene (250 ml) was refluxed for 2 hours under nitrogen. Solvents were removed under vacuum and the remaining residue was dissolved in ethyl acetate (250 ml), washed with 5% sodium bicarbonate solution, dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel, toluene-ethyl acetate, 99:1 to 95:5) gave the title compound (7 g) as a solid; δH (360 MHz, CDCl3) 7.87-7.84 (2H, m), 7.68-7.46 (6H, m), 7.36 (1H, d, J=7.7 Hz), 4.05 (1H, d, J=13.2 Hz), 3.72 (1H, d, J=13.2 Hz), 1.27 (9H, s); m/z (CI) 329 (M-).

Workup

  1. temperaturewas refluxed for 2 hours under nitrogen
  2. customSolvents were removed under vacuum
  3. dissolutionthe remaining residue was dissolved in ethyl acetate (250 ml)
  4. washwashed with 5% sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b90e2062bde84c52963aad867eb3ea04
Source dataset
uspto-grants-1997_10
Patent number
US05681833

Reaction notes

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