Dicyclohexylcarbodiimide → HCID 21188765, compound

HRID 1383979Notes

Reaction equation

HRID 1383979 reaction equation
[C:1]([CH:4]([CH3:26])[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=2[N:9]=[C:8]1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)([OH:3])=O.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[N:27]1([C:1]([CH:4]([CH3:26])[CH2:5][CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=3[N:9]=[C:8]2[CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[O:3])[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 211885121-(3-Carboxybutyl)-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole

Product 1

HCID 21188765HCID 21188765, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of (RS) 1-[3-carboxybutyl]-2-[(4-chlorophenoxy)methyl]-4-methylbenzimidazole (0.700 g, 1.9 mmol) in N,N-dimethylformamide (40 ml) were added sequentially pyrroldine (155 mg, 1.1 eq), 1-hydroxybenzotriazole (282 mg, 1.1 eq), and dicyclohexylcarbodiimide (431 mg, 1.1 eq). The resulting mixture was then stirred under a nitrogen atmosphere at room temperature for 64 hours. The reaction mixture was then filtered and the resulting filtrate was concentrated under reduced pressure. This residue was taken into ethyl acetate (200 ml) and washed once with water (200 ml), dried over potassium carbonate. The solvents were removed in vacuo to yield 0.835 grams of the title product as a white foam.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe resulting filtrate was concentrated under reduced pressure
  3. washwashed once with water (200 ml)
  4. dry with materialdried over potassium carbonate
  5. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-57bda9fcecd8463a9aab80afac138949
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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