1,3-Benzodioxole-5-carboxylic acid → HCID 19050315, compound

HRID 1779263Notes

Reaction equation

HRID 1779263 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH2:13]([C:21]1[CH:22]=[N:23][C:24]([C:27]2[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=2)=[N:25][CH:26]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][C:30]3[CH:29]=[CH:28][C:27]([C:24]4[N:23]=[CH:22][C:21]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:26][N:25]=4)=[CH:32][CH:31]=3)=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 71961,3-Benzodioxole-5-carboxylic acidHCID 10868DicyclohexylcarbodiimideHCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidine

Product 1

HCID 19050315HCID 19050315, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

5 mmol of benzo[1,3]dioxole-5-carboxylic acid and 4.8 mmol of 4-(5-octylpyrimidin-2-yl)phenol are dissolved in 50 ml of CH2Cl2, and 5 mmol of DCC and 0.05 mmol of DMAP are added. The mixture is stirred for 18 hours with exclusion of light, the solvent is stripped off vacuo, and the product is purified by column chromatography on silica gel, giving 4-(5-octylpyrimidin-2-yl)phenyl benzo[1,3]dioxole-5-carboxylate.

Workup

  1. customthe product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-db869f67478f432ebdf51f8b6a95704c
Source dataset
uspto-grants-1997_05
Patent number
US05626791

Reaction notes

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