4-Chloro-2-nitroaniline → 3-Thiophenamine, N-(4-chloro-2-nitrophenyl)tetrahydro-, 1,1-dioxide, (3S)-

HRID 1500859Notes

Reaction equation

HRID 1500859 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[O:12]=[S:13]1(=[O:19])[CH2:17][CH2:16][C@H:15](N)[CH2:14]1.C([O-])([O-])=O.[K+].[K+].CCN(CC)CC>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@H:15]2[CH2:16][CH2:17][S:13](=[O:19])(=[O:12])[CH2:14]2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

7

Reactant 4

HCID 69794-Chloro-2-nitroanilineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 7058659HCID 7058659, compound

Product 1

HCID 295470163-Thiophenamine, N-(4-chloro-2-nitrophenyl)tetrahydro-, 1,1-dioxide, (3S)-Yield 66.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4-chloro-2-nitro-phenylamine (1.2 g, 6.8 mmol) and (S)-1,1-dioxo-tetrahydro-1λ6-thiophen-3-ylamine (0.97 g, 5.7 mmol) and K2CO3 (13.6 mmol) in DMF (8 mL) was added Et3N (13.6 mmol). The mixture was stirred at 100° C. for 2 h. After cooled to RT, the reaction mixture was poured into water, extracted with EtOAc. The organic phase was washed with saturated NH4Cl, aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4. The nitro compound (1.1 g, yield: 66%) was obtained as yellow solid by flash column (ethyl acetate/petroleum ether=1/1). MS obsd. MS obsd. (ESI+) [(M+H)+] 291.0.

Workup

  1. temperatureAfter cooled to RT
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with saturated NH4Cl, aqueous NaHCO3 and brine
  4. dry with materialThe organic phase was dried over Na2SO4

Sources & evidence

ORD record
ord-78ae6121cc98490d891f41477191c95a
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

Loading…