Sodium methanethiolate → HCID 12010658, compound

HRID 1250315Notes

Reaction equation

HRID 1250315 reaction equation
[CH3:1][S-:2].[Na+].[N+]([C:7]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:8]=1[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])([O-])=O>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][S:2][C:7]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:8]=1[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10]

Participants

6

Reactant 2

HCID 4378561Sodium methanethiolateHCID 12010657HCID 12010657, compound

Product 1

HCID 12010658HCID 12010658, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Sodium thiomethoxide (0.91 g; 13.0 mmol; 1.3 equiv) was dissolved in water (3.4 mL). Tetrabutylammonium bromide (0.48 g; 1.50 mmol; 0.15 equiv) was added. Butyl 2-nitro-4-trifluoromethylbenzoate (5b; 2.91 g; 10.0 mmol) was dissolved in toluene (5 mL) and added to the mixture. The reaction mixture was stirred at ambient temperature for 2.5 h to completely consume 5b according to thin layer chromatography (tlc) analysis. The reaction mixture was diluted with toluene and water and the layers were thoroughly mixed and then separated. The organic layer was dried over Na2SO4 and concentrated to afford 2.85 g (98%) of 6b which contained a small amount of tetrabutylammonium bromide. The crude product was flash chromatographed and eluted with 5% ethyl acetate in heptane to afford 2.32 g (79%) of pure 6b.

Workup

  1. additionadded to the mixture
  2. customto completely consume 5b
  3. additionThe reaction mixture was diluted with toluene and water
  4. additionthe layers were thoroughly mixed
  5. customseparated
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-187933176aff415a98298762410540e9
Source dataset
uspto-grants-2002_01
Patent number
US06337418B1

Reaction notes

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