4-Chlorobenzoic Acid → HCID 69429545, compound

HRID 970761Notes

Reaction equation

HRID 970761 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=1.[CH:23]([O:26][C:27]([NH:29][CH:30]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:31][NH2:32])=[O:28])([CH3:25])[CH3:24]>O1CCCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:32][CH2:31][CH:30]([NH:29][C:27]([O:26][CH:23]([CH3:25])[CH3:24])=[O:28])[CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:20])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 63184-Chlorobenzoic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 22935188HCID 22935188, compound

Product 1

HCID 69429545HCID 69429545, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.21 g of 1,1′-carbonylbis-1H-imidazole was added to a solution of 0.19 g of 4-chlorobenzoic acid in tetrahydrofuran and stirred for 1 hour at room temperature. Then 5 ml of a solution of 0.25 g of 2-(i-propoxycarbonylamino)-3-phenylpropylamine in tetrahydrofuran was added to the above solution and stirred at room temperature for 4 hours. The reaction mixture was rinsed with water, the organic layer was dried over magnesium sulfate anhydrous, and the residual oily material obtained under a reduced pressure was purified by column chromatography on silica gel (2:1 hexane/ethyl acetate) to obtain 0.26 g of the title compound as colorless crystals.

Workup

  1. stirringstirred at room temperature for 4 hours
  2. washThe reaction mixture was rinsed with water
  3. dry with materialthe organic layer was dried over magnesium sulfate anhydrous
  4. customthe residual oily material obtained under a reduced pressure
  5. customwas purified by column chromatography on silica gel (2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c3afb6d0f0d24834970cd9c9162a95a3
Source dataset
uspto-grants-2007_12
Patent number
US07312245B2

Reaction notes

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