Dicyclohexylcarbodiimide → HCID 18654211, compound

HRID 1741946Notes

Reaction equation

HRID 1741946 reaction equation
[NH2:1][C:2]1[C:3]([O:14][C@@H:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:23]([C:30]1[CH:31]=[N:32][C:33]([C:36]2[CH:41]=[CH:40][C:39](O)=[CH:38][CH:37]=2)=[N:34][CH:35]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[NH2:1][C:2]1[C:3]([O:14][C@@H:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:16])=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([O:9][C:39]1[CH:38]=[CH:37][C:36]([C:33]2[N:32]=[CH:31][C:30]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:35][N:34]=2)=[CH:41][CH:40]=1)=[O:8]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 54097014HCID 54097014, compoundHCID 1356171522-(4Hydroxyphenyl)-5-n-heptylpyrimidine

Product 1

HCID 18654211HCID 18654211, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

5-Amino-2-nitro-4-[(R)-2-octyloxy]benzoic acid (0.06 g), 0.1 g of 4-(5-heptyl-2-pyrimidinyl)phenol and 0.04 g of 4-(dimethylamino)pyridine were dissolved in 10 ml of dichloromethane and the solution was treated portionwise within 10 minutes with 0.07 g of N,N'-dicyclohexylcarbodiimide while stirring. The mixture was stirred at room temperature for 40 hours, filtered and concentrated. Chromatography of the residue on silica gel with ethyl acetate/dichloromethane (vol. 1:8) and recrystallization from diethyl ether/hexane (vol. 1:1), gave 0.09 g of 4-(5-heptyl-2-pyrimidinyl)phenyl 5-amino-2-nitro-4-[(R)-2-octyloxy]benzoate of melting point 105° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 40 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customChromatography of the residue on silica gel with ethyl acetate/dichloromethane (vol. 1:8) and recrystallization from diethyl ether/hexane (vol. 1:1)

Sources & evidence

ORD record
ord-c66d39da03494d478d901c8e77bbe3a1
Source dataset
uspto-grants-1994_08
Patent number
US05335303

Reaction notes

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