1,2-Dichloroethane → HCID 22119924, compound

HRID 1274628Notes

Reaction equation

HRID 1274628 reaction equation
[Cl:1][CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:37]N1C(=O)CCC1=O.ClCCCl>C(Cl)Cl>[Br:37][CH:2]([Cl:1])[C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimide2×HCID 22119912HCID 22119912, compound

Product 1

HCID 22119924HCID 22119924, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[3-(chloromethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (1.00 g, 0.00266 mol), azo-bis-isobutyronitrile (0.100 g), N-bromosuccinimide (0.712 g, 0.00400 mol) and 1,2-dichloroethane is stirred one hour at reflux. Additional azo-bis-isobutyronitrile (0.0500 g) and N-bromosuccinimide (0.100 g) are added and the mixture is stirred two hours at reflux, cooled to room temperature, diluted with methylene chloride, washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to an orange gum. Chromatography of the gum on silica gel with methylene chloride:ether gives the title compound as a white foam (0.950 g, 80.2%, mp 93-96° C.) which is identified by NMR spectral analysis.

Workup

  1. temperatureat reflux
  2. stirringthe mixture is stirred two hours
  3. temperatureat reflux
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo to an orange gum

Sources & evidence

ORD record
ord-c1210a5abc8d44b898b6346aef5d63cc
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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