1,1'-Carbonyldiimidazole → Benzeneacetamide

HRID 638357Notes

Reaction equation

HRID 638357 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1Cl.C(N1C=CN=C1)([N:15]1C=CN=C1)=O>C(Cl)Cl>[C:4]1([CH2:9][C:10]([NH2:15])=[O:12])[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 798743,4-Dichlorophenylacetic acid

Product 1

HCID 7680BenzeneacetamideYield 176.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.23 g of 3,4-dichlorophenylacetic acid in 200 ml of methylene chloride was treated at 0° with 3.35 g of carbonyldiimidazole. The mixture was stirred for 40 min. Then, 2.86 g (0.0159 mol) of the (+) amine from the resolution which was previously described in Part D, above, was added. The mixture was stirred for 24 hr and partitioned with saturated aqueous sodium bicarbonate. The organic phase was dried and concentrated to yield 4.93 g of the named (-)-benzeneacetamide product which had an [α]D25 -24° (6.75 mg/ml in methanol). The product was dissolved in a minimum volume of methanol and treated with 1.48 g of maleic acid which had been dissolved in a minimum volume of methanol and the mixture was diluted with diethyl ether. The resultant crystals were filtered to yield 5.02 g of the named salt product, mp 167°-169°, [α]D25 -29.7° (10.0 mg/ml in methanol).

Workup

  1. additionabove, was added
  2. stirringThe mixture was stirred for 24 hr
  3. custompartitioned with saturated aqueous sodium bicarbonate
  4. customThe organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-96fb3b270b3a489fa48296475cd714b6
Source dataset
uspto-grants-1985_12
Patent number
US04560767

Reaction notes

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