Sodium Bicarbonate → HCID 117818895, compound

HRID 2206880Notes

Reaction equation

HRID 2206880 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]=1[CH:16]=[CH2:17])(=[O:4])=[O:3].C(=O)([O-])O.[Na+].[Cl:23][CH2:24][C:25](=[O:30])[C:26](Cl)=[N:27][OH:28]>C(#N)C>[CH3:1][S:2]([O:5][C:6]1[CH:11]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:9]=[CH:8][C:7]=1[CH:16]1[O:28][N:27]=[C:26]([C:25](=[O:30])[CH2:24][Cl:23])[CH2:17]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 68330913-chloro-N-hydroxy-2-oxopropanimidoyl chlorideHCID 117818578HCID 117818578, compound

Product 1

HCID 117818895HCID 117818895, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(trifluoromethyl)-2-vinylphenyl methanesulphonate (1.05 g) in acetonitrile (10 ml) were added sodium hydrogencarbonate (2.55 g) and 3-chloro-N-hydroxy-2-oxopropanimidoyl chloride (0.60 g) at room temperature under argon. The reaction mixture was stirred at room temperature for one hour. The solids were filtered off with suction and the filtrate was concentrated under reduced pressure. The residue was stirred with heptane to obtain 2-[3-(chloroacetyl)-4,5-dihydro-1,2-oxazol-5-yl]-5-(trifluoromethyl)phenyl methanesulphonate (1.33 g, 86% pure, 75%).

Workup

  1. filtrationThe solids were filtered off with suction
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. stirringThe residue was stirred with heptane

Sources & evidence

ORD record
ord-7469509ab8c14db791f2f2a0363a6548
Source dataset
uspto-grants-2016_06
Patent number
US09375009B2

Reaction notes

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