1-Hydroxybenzotriazole → 1-[4-(4-Pentylphenyl)cinnamoyl]benzotriazole 3-oxide

HRID 1386596Notes

Reaction equation

HRID 1386596 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[CH2:11]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:32]=[CH:31][C:25]([CH:26]=[CH:27][C:28](O)=[O:29])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[CH2:12][CH2:13][CH2:14][CH3:15].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:11]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:32]=[CH:31][C:25]([CH:26]=[CH:27][C:28]([N:4]3[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[N+:2]([O-:1])=[N:3]3)=[O:29])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 540947814-(4-Pentylphenyl)cinnamic acid

Product 1

HCID 542184911-[4-(4-Pentylphenyl)cinnamoyl]benzotriazole 3-oxideYield 42.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 1-hydroxybenzotriazole (0.20 g) and 4-(4-pentylphenyl)cinnamic acid (0.40 g) in dichloromethane (12.0 ml) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.33 g) (WSCD.HCl), and the mixture was stirred for 12 hours at ambient temperature. The reaction mixture was diluted with dichloromethane, and washed with brine, and dried over magnesium sulfate. After magnesium sulfate was filtered off, evaporation of the filtrate and trituration with acetonitrile gave 1-[4-(4-Pentylphenyl)cinnamoyl]benzotriazole 3-oxide (0.24 g).

Workup

  1. washwashed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter magnesium sulfate was filtered off
  4. customevaporation of the filtrate and trituration with acetonitrile

Sources & evidence

ORD record
ord-78dfb9836640462e831730d095070ccc
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

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