1,1'-Carbonyldiimidazole → HCID 15123258, compound

HRID 1196528Notes

Reaction equation

HRID 1196528 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[N:25]1([CH2:30][CH:31]2[NH:36][CH2:35][CH:34]([OH:37])[CH2:33][CH2:32]2)[CH2:29][CH2:28][CH2:27][CH2:26]1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:36]2[CH:31]([CH2:30][N:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)[CH2:32][CH2:33][CH:34]([OH:37])[CH2:35]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 798743,4-Dichlorophenylacetic acidHCID 15123257HCID 15123257, compound

Product 1

HCID 15123258HCID 15123258, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 3,4-dichlorophenylacetic acid (0.64 g) in dry dichloromethane (15 ml) was treated with 1,1'-carbonyldiimidazole (0.51 g) portionwise over a 5 minute period. The mixture was stirred at ambient temperature for 40 min and was added to a solution of the product of stage (ii) (0.55 g) in dichloromethane (20 ml). The reaction mixture was stirred at ambient temperature for 18 h, diluted with dichloromethane (50 ml) and washed with aqueous sodium carbonate solution (2M; 2×10 ml). The organic extract was dried, filtered, and evaporated in vacuo to give an oily residue (1.1 g). The residue was purified by flash chromatography using dichloromethane methanol/ammonia (200:8:1) as eluent to give the title compound as an oil (0.32 g). T.l.c. Silica(dichloromethane/methanol/ammonia 150:8:1) Rf 0.5.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 18 h
  2. washwashed with aqueous sodium carbonate solution (2M; 2×10 ml)
  3. extractionThe organic extract
  4. customwas dried
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8f2ce3dae30749bb825588bf20467565
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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