1-Bromo-2-Chloroethane → HCID 12761371, compound

HRID 424585Notes

Reaction equation

HRID 424585 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[OH-].[Na+].Br[CH2:12][CH2:13][Cl:14]>C(O)C.O.C(OCC)(=O)C>[Cl:14][CH2:13][CH2:12][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

7

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 87132-AminothiophenolHCID 14798Sodium Hydroxide

Product 1

HCID 12761371HCID 12761371, compoundYield 97.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-aminobenzenethiol (0.513 mL, 4.79 mmol) in ethanol (5 mL) was added sodium hydroxide (192 mg, 4.79 mmol) as a solution in water (5.00 mL). To the resulting mixture was added 1-bromo-2-chloroethane (1.197 mL, 14.38 mmol), and the resulting mixture was stirred vigorously for 20 minutes 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 yellow liquid, 2-(2-chloroethylthio)aniline (875 mg, 97%). 1H NMR (DMSO-d6) δ 7.27 (d, J=7.5 Hz, 1H), 7.10-7.04 (m, 1H), 6.73 (d, J=8.1 Hz, 1H), 6.56-6.49 (m, 1H), 5.41 (brs, 2H), 3.62 (t, J=7.4 Hz, 2H), 3.02 (t, J=7.4 Hz, 2H). ESI-MS (m/z, %): 188 (MH+, 100).

Workup

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

Sources & evidence

ORD record
ord-0df13f9aca924ca2a953969e797cc424
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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