2-Mercaptoethanol → 2-(2-Amino-5-fluoro-4-nitrophenylthio)ethanol

HRID 424593Notes

Reaction equation

HRID 424593 reaction equation
F[C:2]1[CH:8]=[C:7]([F:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].[SH:19][CH2:20][CH2:21][OH:22]>CN(C=O)C.C(OCC)(=O)C>[NH2:4][C:3]1[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[C:7]([F:9])=[CH:8][C:2]=1[S:19][CH2:20][CH2:21][OH:22]

Participants

6

Reactant 3

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 27583122,4-Difluoro-5-nitroaniline

Product 1

HCID 591440992-(2-Amino-5-fluoro-4-nitrophenylthio)ethanolYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred suspension of 2,4-difluoro-5-nitroaniline (100 mg, 0.574 mmol) and potassium carbonate (159 mg, 1.149 mmol) in DMF (1 mL) was added 2-mercaptoethanol (0.081 mL, 1.149 mmol). The resulting mixture was stirred at room temperature for 2 hours. The mixture was then diluted with ethyl acetate and washed with saturated sodium carbonate (3×). The organic phase was dried, filtered, concentrated, and then chromatographed (1:1 EtOAc:hexanes) to give the major product. Ethyl acetate was then used as the eluent to give a minor product. The major product was determined to be the desired product (112 mg, 84%). 1H NMR (DMSO-d6) δ 7.32 (d, J=3.5 Hz, 1H), 7.27 (d, J=10.7 Hz, 1H), 4.39 (s, 2H), 3.85-3.76 (m, 2H), 3.16-3.08 (m, 2H), 2.13-2.05 (m, 1H); ESI-MS (m/z, %): 233 (MH+, 100), 215 (14), 187 (100), 129 (65).

Workup

  1. washwashed with saturated sodium carbonate (3×)
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (1:1 EtOAc:hexanes)
  6. customto give the major product
  7. customto give a minor product

Sources & evidence

ORD record
ord-aa2aa841135a4453946559194a97f6a1
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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