Dimethylformamide → (4-Dimethylthiocarbamoyloxy-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester

HRID 238630Notes

Reaction equation

HRID 238630 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH3:29][N:30]([CH3:34])[C:31](Cl)=[S:32]>O>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][C:31](=[S:32])[N:30]([CH3:34])[CH3:29])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:16])[CH:11]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27871Dimethylthiocarbamoyl chlorideHCID 20335012(6-Fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester

Product 1

HCID 59326495(4-Dimethylthiocarbamoyloxy-6-fluoro-naphthalen-2-yl)-acetic acid methyl esterYield 71.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (500 mg, 2.14 mmol), finely ground potassium carbonate (591 mg, 4.28 mmol), and N,N-dimethylformamide (10 mL) was stirred at room temperature for 20 minutes. Dimethylthiocarbamoyl chloride (290 mg, 2.35 mmol) was added in one portion. After being stirred for 2 hours, the resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate (20 mL×2). The combined organic layers were washed with water (15 mL) and brine (20 mL), then dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (gradient elution with 0-30% ethyl acetate in hexanes) to afford (4-dimethylthiocarbamoyloxy-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (491 mg, 71.5%) as a yellow oil.

Workup

  1. stirringAfter being stirred for 2 hours
  2. extractionextracted with ethyl acetate (20 mL×2)
  3. washThe combined organic layers were washed with water (15 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (gradient elution with 0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-016f8699d7344e008b3ff582dafa930f
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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