P-Toluenesulfonamide → 2-Acetylamino-5-[1-(ethoxycarbonyl-hydrazono)-ethyl]-4-trifluoromethyl-benzoic acid methyl ester

HRID 906627Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=O)[CH3:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17][C:18](=[O:20])[CH3:19].[CH2:22]([O:24][C:25](=[O:28])[NH:26][NH2:27])[CH3:23].CC1C=CC(S(N)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[N:27][NH:26][C:25]([O:24][CH2:22][CH3:23])=[O:28])[CH3:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17][C:18](=[O:20])[CH3:19]

Participants

Conditions

Temperature: 150 °C

Procedure

In a round bottom flask fitted with a Dean-Stark, a solution of 5-acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl ester (2.384 g, 7.86 mmol) in toluene (16 mL) was treated with ethylcarbazate (2.61 g, 25 mmol,) followed by p-toluenesulfonamide (103 mg, 0.60 mmol). The reaction was stirred at 150° C. for 40 h. The solvent was removed by distillation and the residue was purified by flash column chromatography (silica gel, 1:1 EtOAc/hexanes) to give the title compound (1.24 g, 40%). API-ES: m/z 390.1 [M+H]+, rt 4.14 min, 4.20 min: mixture of cis and trans.

Workup

customIn a round bottom flask fitted with a Dean-Stark
customThe solvent was removed by distillation
customthe residue was purified by flash column chromatography (silica gel, 1:1 EtOAc/hexanes)

Sources & evidence

ORD record: ord-d53f57b4260d43088be39f389ce8ce6f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012988B2

Reaction notes

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