1,1'-Carbonyldiimidazole → Benzeneacetamide

HRID 638359Notes

Reaction equation

HRID 638359 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 7680Benzeneacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.23 g of 3,4-dichlorophenylacetic acid in 200 ml of methylene chloride is treated at 0° C. with 3.35 g of carbonyldiimidazole. The mixture is stirred for 40 minutes. Then 2.86 g (0.0159 mole) of the (±)-amine from Example 1, Part C, above, is added. The mixture is stirred for 24 hr and partitioned with saturated aqueous sodium bicarbonate. The organic phase is dried and concentrated to yield the titled (±)-benzeneacetamide product free base which is dissolved in a minimum volume of methanol and treated with one equivalent of maleic acid which has been dissolved in a minimum volume of methanol and the mixture is diluted with diethyl ether to give the titled maleate salt, mp 152°-155° C.

Workup

  1. stirringThe mixture is stirred for 24 hr
  2. custompartitioned with saturated aqueous sodium bicarbonate
  3. customThe organic phase is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bd80545bd8194988ad6cbe7e41ac5d16
Source dataset
uspto-grants-1985_12
Patent number
US04560767

Reaction notes

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