Water → S-4-benzyl-2-nitrophenyl dimethylcarbamothioate

HRID 2075252Notes

Reaction equation

HRID 2075252 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11](O)=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20][N:21]([CH3:25])[C:22](Cl)=[S:23].[OH2:26]>CN(C=O)C>[CH3:20][N:21]([CH3:25])[C:22](=[O:26])[S:23][C:11]1[CH:12]=[CH:13][C:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27871Dimethylthiocarbamoyl chlorideHCID 7863744-Benzyl-2-nitrophenol

Product 1

HCID 58415382S-4-benzyl-2-nitrophenyl dimethylcarbamothioate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a yellow solution of 4-benzyl-2-nitrophenol (2.0 g, 8.7 mmol) in 20 mL DMF at 0° C. was added sodium hydride (0.38 g, 9.6 mmol). The reaction became deep orange, and after 30 min dimethylthiocarbamoyl chloride (1.2 g, 9.6 mmol) was added. The reaction was stirred over the weekend at room temperature. Water was added, and the mixture was extracted with DCM 3 times. The combined extracts were washed with 0.5M NaHCO3, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a brown oil. The oil was heated to 160° C. for a total of 2 h. The reaction was cooled, and the resulting oil was loaded directly onto a 120 g ISCO column and eluted with 0-30-50% EtOAc/hexanes, to give S-4-benzyl-2-nitrophenyl dimethylcarbamothioate. MS (ESI) m/z: Calculated: 316.1; Observed: 317.1 (M++1).

Workup

  1. extractionthe mixture was extracted with DCM 3 times
  2. washThe combined extracts were washed with 0.5M NaHCO3
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. temperatureThe oil was heated to 160° C. for a total of 2 h
  8. temperatureThe reaction was cooled
  9. washeluted with 0-30-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-1f4cc8af0ed14eaeb808e03e1bc7e0bb
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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