Dicyclohexylcarbodiimide → HCID 15296921, compound

HRID 2210883Notes

Reaction equation

HRID 2210883 reaction equation
[Br:1][CH:2]([C:6]1[N:7]=[N:8][N:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:10]=1)[C:3]([OH:5])=O.[CH:23]([C:26]1[CH:32]=[CH:31][CH:30]=[C:29]([CH:33]([CH3:35])[CH3:34])[C:27]=1[NH2:28])([CH3:25])[CH3:24].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH:33]([C:29]1[CH:30]=[CH:31][CH:32]=[C:26]([CH:23]([CH3:25])[CH3:24])[C:27]=1[NH:28][C:3](=[O:5])[CH:2]([C:6]1[N:7]=[N:8][N:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:10]=1)[Br:1])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 32484DiisopropylanilineHCID 15296920HCID 15296920, compound

Product 1

HCID 15296921HCID 15296921, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of α-bromo-2-dodecyltetrazoleacetic acid (5.0 g, 13.3 mmol) in dichloromethane (75 mL), cooled to -10° C., were added 2,6-diisopropylaniline (2.3 g, 12.9 mmol) and DCC (2.7 g, 13 mmol), respectively. The suspension was gradually warmed to room temperature and was stirred for 12 hours. The mixture was filtered and the filtrate was concentrated in vacuo leaving a yellow liquid. The crude product was purified using silica gel chromatography (elution with 10% ethyl acetate/90% hexane) to give (±)-N-(2,6-diisopropylphenyl) -2-(2-dodecyl-2H-tetrazol-5-yl)-2-bromo-acetamide (4.8 g, 65% ) as a colorless liquid which crystallized on standing;

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customleaving a yellow liquid
  4. customThe crude product was purified
  5. washsilica gel chromatography (elution with 10% ethyl acetate/90% hexane)

Sources & evidence

ORD record
ord-43d39e22ba7e43bfa6a6b8bb306b9ae6
Source dataset
uspto-grants-1995_10
Patent number
US05461049

Reaction notes

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