Sodium hydride → 5-{3-[2-(Ethoxycarbonyl)-1-trifluoromethyl-vinyl]ureido}-6-fluoro-3-(2-propynyl)-2-benzothiazolinone

HRID 2253576Notes

Reaction equation

HRID 2253576 reaction equation
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].[F:15][C:16]1[C:28]([N:29]=[C:30]=[O:31])=[CH:27][C:19]2[N:20]([CH2:24][C:25]#[CH:26])[C:21](=[O:23])[S:22][C:18]=2[CH:17]=1>CN(C)C=O.CN(C)C=O.C1(C)C=CC=CC=1>[CH2:7]([O:6][C:4]([CH:3]=[C:2]([NH:1][C:30](=[O:31])[NH:29][C:28]1[C:16]([F:15])=[CH:17][C:18]2[S:22][C:21](=[O:23])[N:20]([CH2:24][C:25]#[CH:26])[C:19]=2[CH:27]=1)[C:9]([F:10])([F:11])[F:12])=[O:5])[CH3:8]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 143064826-Fluoro-5-isocyanato-3-propargyl-2-benzothiazolone

Product 1

HCID 539264135-{3-[2-(Ethoxycarbonyl)-1-trifluoromethyl-vinyl]ureido}-6-fluoro-3-(2-propynyl)-2-benzothiazolinone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21735183Dimethylformamide tolueneSolvent

Procedure

A solution of 18.51 g of ethyl 3-amino-4,4,4-trifluorocrotonate in 50 ml of dimethylformamide is added dropwise while stirring at 0° C. during 30 minutes to 4.41 g of a 55% sodium hydride dispersion in 100 ml of dimethylformamide and the mixture is stirred at room temperature for 2 hours. The reaction mixture is then cooled to -55° C. and treated during 3 minutes while stirring with a solution of 25.10 g of 6-fluoro-5-isocyanato-3-(2-propynyl)-2-benzothiazolinone in 200 ml of dimethylformamide/toluene (1:1). In so doing, the temperature of the reaction mixture rises to -15° C. and the mixture is subsequently stirred at room temperature for one hour. The thus-formed intermediate 5-{3-[2-(ethoxycarbonyl)-1-trifluoromethyl-vinyl]ureido}-6-fluoro-3-(2-propynyl)-2-benzothiazolinone is not isolated.

Workup

  1. temperatureThe reaction mixture is then cooled to -55° C.
  2. additiontreated during 3 minutes
  3. customrises to -15° C.
  4. stirringthe mixture is subsequently stirred at room temperature for one hour

Sources & evidence

ORD record
ord-a668c75a2ae9484f88f299ccb7a71d3b
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

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