4-Nitrophenol → Methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid 4-nitrophenyl ester

HRID 427292Notes

Reaction equation

HRID 427292 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[S:11][C:7]=2[C:6]([C:16]([OH:18])=[O:17])=[CH:5][CH:4]=1.[CH:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21](O)[CH:20]=1.CN(C1C=CC=CN=1)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[N+:25]([C:24]1[CH:19]=[CH:20][C:21]([O:17][C:16]([C:6]2[C:7]3[S:11][C:10]([C:12]([F:13])([F:14])[F:15])=[N:9][C:8]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:18])=[CH:22][CH:23]=1)([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183569954-Methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid

Product 1

HCID 69689660Methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid 4-nitrophenyl esterYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid (140 mg) in dichloromethane (10ml) was treated with p-nitrophenol (72 mg), dimethylaminopyridine (catalytic) and 1-(3-dimethylaminopropyl)-3-ethyl carbodimide hydrochloride (150 mg). The mixture was stirred at room temperature for 12 hours and the reaction washed with water (10 ml). The organic layer was separated, dried over magnesium sulphate (5 g) and evaporated in vacuo. Purification by flash chromatography (eluent 50% ethyl acetate/hexane) yielded the title compound as an off-white solid (150 mg). TLC Rf 0.13 (50% ethyl acetate in heptane).

Workup

  1. washthe reaction washed with water (10 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulphate (5 g)
  4. customevaporated in vacuo
  5. customPurification by flash chromatography (eluent 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4a57574299c14853ba29b6f739adcca7
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

Loading…