Triethylamine → 3-Chloro-2,2-dimethyl-N-[2-nitro-4-(trifluoromethyl)phenyl]propanamide

HRID 2115896Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[NH2:14])([O-:3])=[O:2].[Cl:15][CH2:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19].C(N(CC)CC)C>C(Cl)Cl>[Cl:15][CH2:16][C:17]([CH3:22])([CH3:21])[C:18]([NH:14][C:5]1[CH:6]=[CH:7][C:8]([C:10]([F:11])([F:12])[F:13])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])=[O:19]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-nitro-4-(trifluoromethyl)benzenamine (3.00 g, 14.9 mmol, 1.0 equiv) in CH2Cl2 (90 mL) at 25° C., was added 3-chloro-2,2-dimethylpropanoyl chloride (3.9 mL, 29.8 mmol, 2.0 equiv) followed by triethylamine (4.2 mL, 29.8 mmol, 2.0 equiv). The solution was heated to 40° C. After 48 h, the solution was washed with water (50 mL), and brine (50 mL). After concentration in vacuo, the residue was purified by silica gel chromatography (1:10 hexanes:EtOAc to 1:5 hexanes:EtOAc) to afford 3-chloro-2,2-dimethyl-N-(2-nitro-4-(trifluoromethyl)phenyl)propanamide. MS-No (MH+) observed.

Workup

washthe solution was washed with water (50 mL), and brine (50 mL)
concentrationAfter concentration in vacuo
customthe residue was purified by silica gel chromatography (1:10 hexanes:EtOAc to 1:5 hexanes:EtOAc)

Sources & evidence

ORD record: ord-969a781cdbd74be78d9a58271c218ca0
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435823B2

Reaction notes

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