Phenylacetyl chloride → HCID 67916020, compound

HRID 1029948Notes

Reaction equation

HRID 1029948 reaction equation
Cl.[C:2]1([CH3:25])[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2([C:18]3[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[CH:16]3[CH:12]([CH2:13][NH:14][CH2:15]3)[C:11](=[O:17])[CH2:10][CH2:9]2)[CH:3]=1.C(N(CC)CC)C.[C:33]1([CH2:39][C:40](Cl)=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[C:2]1([CH3:25])[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2([C:18]3[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[CH:16]3[CH:12]([CH2:13][N:14]([C:40](=[O:41])[CH2:39][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:15]3)[C:11](=[O:17])[CH2:10][CH2:9]2)[CH:3]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 67915919HCID 67915919, compound

Product 1

HCID 67916020HCID 67916020, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of (3aRS,7aRS)-7,7-bis-(3-tolyl)-4-perhydroisoindolone hydrochloride (1.5 g) in dichloromethane (30 cc) cooled to +4° C. is treated with triethylamine (1.15 cc) and then with phenylacetyl chloride (0.63 g). The reaction mixture is stirred for 5 hours at 25° C. and then washed with water (3×100 cc). The organic phase is dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized twice from acetonitrile to give (3aRS,7aRS)-7,7-bis-(3-tolyl)-2-(phenylacetyl)-4-perhydroisoindolone (0.36 g). m.p.=207° C.

Workup

  1. temperaturecooled to +4° C.
  2. washwashed with water (3×100 cc)
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is crystallized twice from acetonitrile

Sources & evidence

ORD record
ord-d9e78980a31749f582720bbe11a8cc45
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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