2-Mercaptoethanol → 2-(2-Amino-4-nitrophenylthio)ethanol

HRID 1917205Notes

Reaction equation

HRID 1917205 reaction equation
Cl[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].[SH:18][CH2:19][CH2:20][OH:21]>CN(C=O)C.C(OCC)(=O)C>[NH2:4][C:3]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:2]=1[S:18][CH2:19][CH2:20][OH:21]

Participants

6

Reactant 3

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 226912-Chloro-5-nitroaniline

Product 1

HCID 591441672-(2-Amino-4-nitrophenylthio)ethanolYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-chloro-5-nitroaniline (1.0 g, 5.79 mmol) in DMF (10 mL) was added potassium carbonate (1.60 g, 11.59 mmol) followed by 2-mercaptoethanol (0.813 mL, 11.59 mmol). The resulting mixture was then heated at 60° C. for 2 hours and then at room temperature overnight. The mixture was then diluted with ethyl acetate and washed with water (3×), 1N NaOH, and brine. The organic phase was dried, filtered, and concentrated, giving a red/orange solid (1.19 g, 96%). 1H NMR (DMSO-d6) δ 7.52 (s, 1H), 7.42-7.33 (m, 2H), 5.79 (s, 2H), 4.99 (t, J=5.4 Hz, 1H), 3.55 (q, J=6.2 Hz, 2H), 3.02 (t, J=6.6 Hz, 2H); ESI-MS (m/z, %): 215 (MH+, 23), 169 (100), 111 (63).

Workup

  1. customat room temperature
  2. customovernight
  3. washwashed with water (3×), 1N NaOH, and brine
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7c706c1641484a09b6f6ae571ba19a48
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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