1,1'-Carbonyldiimidazole → Benzeneacetamide

HRID 638358Notes

Reaction equation

HRID 638358 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:4]1([CH2:9][C:10]([NH2:15])=[O:12])[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

3

Reactant 2

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

Product 1

HCID 7680Benzeneacetamide

Procedure

In a similar manner, 4.40 g of 3,4-dichlorophenylacetic acid, 3.47 g of carbonyldiimidazole and 2.97 g of the (-) amine from Part D, above, were reacted to yield the above-named (+)-benzeneacetamide product. This product was chromatographed on silica gel (2% methanol (which was saturated with ammonia gas)/98% ethyl acetate) to yield 3.22 g of pure benzeneacetamide product, [α]D25 +34° (8.2 mg/ml in methanol). This benzeneacetamide product was treated with 1.011 g of maleic acid in methanol and the mixture was diluted with diethyl ether to yield 3.56 g of the above named product salt, mp 174°-175° C., [α]D25 +35.3° (10.0 mg/ml in methanol).

Sources & evidence

ORD record
ord-a4deb239dd614143a1dfedd30d8b7e48
Source dataset
uspto-grants-1985_12
Patent number
US04560767

Reaction notes

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