1-Hydroxybenzotriazole → N-[3-(2-hydroxyethyl)phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide

HRID 734580Notes

Reaction equation

HRID 734580 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[CH3:11][C:12]1[S:13][C:14]([C:18](O)=[O:19])=[C:15]([CH3:17])[N:16]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[OH:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([NH:1][C:18]([C:14]2[S:13][C:12]([CH3:11])=[N:16][C:15]=2[CH3:17])=[O:19])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 736488Dimethyl-1,3-thiazole-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 149389872-(3-Aminophenyl)ethan-1-ol

Product 1

HCID 57444343N-[3-(2-hydroxyethyl)phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamideYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3-Aminophenyl)ethanol (1.202 g, 8.76 mmol) was added to a solution of 2,4-dimethyl-1,3-thiazole-5-carboxylic acid (1.652 g, 10.51 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.015 g, 10.51 mmol) and 1-hydroxybenzotriazole (1.420 g, 10.51 mmol) in dry DMF (20 mL). The mixture was stirred for 14 h then the DMF was removed under reduced pressure and the residue was partitioned between DCM and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel, eluting with ethyl acetate-cyclohexane (1:1 to 1:0) affording the title compound in 73% yield (1.772 g).

Workup

  1. customthe DMF was removed under reduced pressure
  2. customthe residue was partitioned between DCM and saturated aqueous sodium hydrogencarbonate solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude compound was purified by flash chromatography on silica gel
  6. washeluting with ethyl acetate-cyclohexane (1:1 to 1:0)

Sources & evidence

ORD record
ord-78aa114c98d144d286d84b5904225698
Source dataset
uspto-grants-2009_09
Patent number
US07592346B2

Reaction notes

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