4-Nitrophenol → 2-Cyclopropyl-4-methoxybenzothiazole-7-carboxylic acid 4-nitrophenyl ester

HRID 427293Notes

Reaction equation

HRID 427293 reaction equation
[CH:1]1([C:4]2[S:5][C:6]3[C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=[C:9]([O:16][CH3:17])[C:7]=3[N:8]=2)[CH2:3][CH2:2]1.[CH:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[C:20](O)[CH:19]=1.Cl.CN(C)CCCN=C=NCC.C(OCC)C>ClCCl>[N+:24]([C:23]1[CH:18]=[CH:19][C:20]([O:14][C:13]([C:12]2[C:6]3[S:5][C:4]([CH:1]4[CH2:2][CH2:3]4)=[N:8][C:7]=3[C:9]([O:16][CH3:17])=[CH:10][CH:11]=2)=[O:15])=[CH:21][CH:22]=1)([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 3283Diethyl EtherHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183570082-Cyclopropyl-4-methoxybenzothiazole-7-carboxylic acid

Product 1

HCID 696906902-Cyclopropyl-4-methoxybenzothiazole-7-carboxylic acid 4-nitrophenyl esterYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Starting from 2-cyclopropyl-4-methoxybenzothiazole-7-carboxylic acid (270 mg), p-nitrophenol (165 mg), and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (228 mg) in dichloromethane (35 ml). Trituration ofthe residue with diethyl ether yielded the title compound as a bright yellow solid (290 mg). TLC Rf 0.60 (ethyl acetate).

Sources & evidence

ORD record
ord-702aba683958496691c97b925030b450
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

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