1,1,1,2-Tetrachloroethane → HCID 22120005, compound

HRID 1274629Notes

Reaction equation

HRID 1274629 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:17]=3[CH:26]=2)[C:3]1=[O:27].[Br:28]N1C(=O)CCC1=O.ClCC(Cl)(Cl)Cl>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][N:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH:21]([Br:28])[C:22]([O:24][CH3:25])=[O:23])[C:17]=3[CH:26]=2)[C:3]1=[O:27]

Participants

5

Reactant 3

HCID 124181,1,1,2-TetrachloroethaneHCID 67184N-bromobutanimideHCID 22119857HCID 22119857, compound

Product 1

HCID 22120005HCID 22120005, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 7187Benzoyl PeroxideCatalyst

Procedure

A mixture of methyl 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate (0.400 g, 0.00100 mol), N-bromosuccinimide (0.370 g, 0.00210 mol), benzoyl peroxide (0.0100 g) and tetrachloroethane is stirred 2.5 hours at reflux, cooled to room temperature, and chromatographed on silica gel with methylene chloride to afford the title compound as an off-white solid (0.430 g, 90.0%, mp 84-87° C.) which is identified by NMR spectral analysis.

Workup

  1. temperatureat reflux
  2. customchromatographed on silica gel with methylene chloride

Sources & evidence

ORD record
ord-bbca5a7878264b69a681f1711353cc20
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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