4-Nitrophenol → 2-(Piperidin-1-yl)-4-methoxybenzothiazole-7-carboxylic acid 4-nitrophenyl ester

HRID 427294Notes

Reaction equation

HRID 427294 reaction equation
[N:1]1([C:7]2[S:8][C:9]3[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[C:10]=3[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[C:23](O)[CH:22]=1.Cl.CN(C)CCCN=C=NCC>ClCCl>[N+:27]([C:26]1[CH:21]=[CH:22][C:23]([O:17][C:16]([C:15]2[C:9]3[S:8][C:7]([N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[N:11][C:10]=3[C:12]([O:19][CH3:20])=[CH:13][CH:14]=2)=[O:18])=[CH:24][CH:25]=1)([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183569982-(Piperidin-1-yl)-4-methoxybenzothiazole-7-carboxylic acid

Product 1

HCID 696911182-(Piperidin-1-yl)-4-methoxybenzothiazole-7-carboxylic acid 4-nitrophenyl esterYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Starting from 2-(piperidin-1-yl)-4-methoxybenzothiazole-7-carboxylic acid (190 mg), p-nitrophenol (100 mg), and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (150 mg) in dichloromethane (20 ml). Purification by column chromatography (eluent 50% ethylacetate in hexane) yielded the title compound as an off-white solid (240 mg). TLC Rf 0.39 (50% ethyl acetate in hexane).

Workup

  1. customPurification by column chromatography (eluent 50% ethylacetate in hexane)

Sources & evidence

ORD record
ord-194e90f9cb9d4cffb94228149b59a5c9
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

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