1-Hydroxybenzotriazole → 4-[2-(4-Pentyloxyphenyl)-thiazol-5-yl]benzoic acid benzotriazol-1-yl ester

HRID 2270049Notes

Reaction equation

HRID 2270049 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]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[S:24][C:25]([C:28]3[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=3)=[CH:26][N:27]=2)=[CH:19][CH:18]=1)[CH2:12][CH2:13][CH2:14][CH3:15].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[N:2]1([O:1][C:32](=[O:33])[C:31]2[CH:30]=[CH:29][C:28]([C:25]3[S:24][C:23]([C:20]4[CH:21]=[CH:22][C:17]([O:16][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:18][CH:19]=4)=[N:27][CH:26]=3)=[CH:36][CH:35]=2)[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183310784-[2-(4-Pentyloxyphenyl)thiazol-5-yl]benzoic acid

Product 1

HCID 536578594-[2-(4-Pentyloxyphenyl)-thiazol-5-yl]benzoic acid benzotriazol-1-yl esterYield 58.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-hydroxybenzotriazole (722 mg) and 4-[2-(4-pentyloxyphenyl)thiazol-5-yl]benzoic acid (1.64 g) in dichloromethane (33 ml) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (WSC.HCl) (1.28 g), and stirred for 2 hours at ambient temperature. To the reaction mixture was added dichloromethane (500 ml) to be clear solution, then washed with water (200 ml×2) and brine, and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The solids were slurried in acetonitrile, and collected by filtration to give 4-[2-(4-pentyloxyphenyl)-thiazol-5-yl]benzoic acid benzotriazol-1-yl ester (1.27 g).

Workup

  1. washwashed with water (200 ml×2) and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationMagnesium sulfate was filtered off
  4. customthe filtrate was evaporated under reduced pressure
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a8643344fb0641e1bc19df643789e5e3
Source dataset
uspto-grants-2001_12
Patent number
US06331521B1

Reaction notes

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