1-Bromo-2-Chloroethane → 2-(2-Chloroethylthio)-4-nitroaniline

HRID 424498Notes

Reaction equation

HRID 424498 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[SH:11].[OH-].[Na+].Br[CH2:15][CH2:16][Cl:17]>C(O)C.O.C(OCC)(=O)C>[Cl:17][CH2:16][CH2:15][S:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

7

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 109866912-Amino-5-nitrobenzenethiol

Product 1

HCID 591440982-(2-Chloroethylthio)-4-nitroanilineYield 91.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 2-amino-5-nitrobenzenethiol (4.11 g, 24.15 mmol) in ethanol (50 mL) and water (10 mL) was added sodium hydroxide (0.966 g, 24.15 mmol). To the resulting solution was added 1-bromo-2-chloroethane (8.04 mL, 97 mmol), and the resulting mixture was stirred at room temperature for 3 hours. The mixture was then diluted with ethyl acetate and washed with saturated sodium carbonate (3×). The organic phase was dried, filtered, and concentrated, giving a dark yellow solid (5.13 g, 91%). 1H NMR (DMSO-d6) δ 8.16 (d, J=2.7 Hz, 1H), 7.97 (dd, J=9.0, 2.7 Hz, 1H), 6.94 (brs, 2H), 6.79 (d, J=9.0 Hz, 1H), 3.68 (t, J=7.2 Hz, 2H), 3.11 (t, J=7.2 Hz, 2H); ESI-MS (m/z, %): 233 (MH+, 100), 216 (79).

Workup

  1. washwashed with saturated sodium carbonate (3×)
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-be1aa9b205624d7a8a64977b9bfd69fe
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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