Dicyclohexylcarbodiimide → N-[2,6-bis(1-methylethyl)phenyl]-5-decyl-2H-tetrazole-2-acetamide

HRID 264078Notes

Reaction equation

HRID 264078 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].[CH2:14]([C:24]1[N:25]=[N:26][N:27]([CH2:29][C:30](O)=[O:31])[N:28]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH3:12][CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH:6][C:30](=[O:31])[CH2:29][N:27]1[N:26]=[N:25][C:24]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[N:28]1)[CH3:13]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 32484DiisopropylanilineHCID 214695295-decyl-2H-tetrazole-2-acetic acid

Product 1

HCID 21469460N-[2,6-bis(1-methylethyl)phenyl]-5-decyl-2H-tetrazole-2-acetamideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,6-diisopropyl aniline (0.97 g, 0.006 mol) and 5-decyl-2H-tetrazole-2-acetic acid (1.47 g, 0.006 mol) in 100 mL dichloromethane was cooled to 0° C. under an atmosphere of nitrogen. Solid DCC (1.19 g, 0.006 mol) was added in one portion and the resulting suspension was warmed to room temperature and stirred for 16 hours. Concentrated in vacuo and triturated the residue with diethyl ester. Filtered to remove the dicyclohexyl urea by-product. Concentrated the filtrate and triturated with hexanes to give the title compound (2.02 g, 86%) as an off-white solid, mp 108°-110° C.

Workup

  1. concentrationConcentrated in vacuo
  2. customtriturated the residue with diethyl ester
  3. filtrationFiltered
  4. customto remove the dicyclohexyl urea by-product
  5. concentrationConcentrated the filtrate
  6. customtriturated with hexanes

Sources & evidence

ORD record
ord-8c6b8a3334de4a24b9f1f83a010a025a
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Reaction notes

Loading…