Sodium hydride → 5-Bromo-2-dimethylthiocarbamoyloxy-3-nitro-benzoic acid ethyl ester
Reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[C:8]=1[OH:17])[CH3:4].[H][H].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[S:24]>CN(C=O)C>[CH2:3]([O:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([Br:13])[CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[C:8]=1[O:17][C:23](=[S:24])[N:22]([CH3:26])[CH3:21])[CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of NaH (760 mg, 40%, 19 mmol) in DMF (50 mL) is added the 5-Bromo-2-hydroxy-3-nitro-benzoic acid ethyl ester (4.22 g, 18.2 mmol) portionwise over 5 minutes. After all the hydrogen gas is evolved the reaction is stirred for an additional 10 minutes and then an additional 100 mL, of dry DMF is added. The reaction is stirred at room temperature for 1 minute and dimethylthiocarbamoyl chloride (2.4 g, 18.9 mmol) is added over 5 minutes (Caution stench). The resulting reaction is stirred at room temperature for three days and then checked for completion by LC/MS. Reaction is quenched with water and extracted with ethyl acetate and dichloromethane to give 5.2 g (90%) of the crude product 80% pure, used without further purification. LCMS (ESMS): m/z 378.3 (M+H+).
Workup
- stirringThe reaction is stirred at room temperature for 1 minute
- customThe resulting reaction
- stirringis stirred at room temperature for three days
- customReaction
- customis quenched with water
- extractionextracted with ethyl acetate and dichloromethane
Sources & evidence
- ORD record
- ord-b76fafc688e646b4b5f7f5401b67cbac
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150556B2
Reaction notes
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