Carbon tetrabromide → HCID 22119875, compound

HRID 1274631Notes

Reaction equation

HRID 1274631 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[CH3:25][N:26]1[C:31]([C:32]([F:35])([F:34])[F:33])=[CH:30][C:29](=[O:36])[N:28]([C:37]2[CH:38]=[CH:39][C:40]3[S:44][N:43]=[C:42]([CH:45]=O)[C:41]=3[CH:47]=2)[C:27]1=[O:48]>C(Cl)Cl>[Br:21][C:20]([Br:24])=[CH:45][C:42]1[C:41]2[CH:47]=[C:37]([N:28]3[C:29](=[O:36])[CH:30]=[C:31]([C:32]([F:35])([F:34])[F:33])[N:26]([CH3:25])[C:27]3=[O:48])[CH:38]=[CH:39][C:40]=2[S:44][N:43]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

Product 1

HCID 22119875HCID 22119875, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphenylphosphine (0.354 g, 0.00138 mol) is added to a solution of carbon tetrabromide (0.223 g, 0.000676 mol) in methylene chloride. The resultant mixture is stirred at room temperature for 10 minutes and treated dropwise with a solution of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde (0.200 g, 0.000563 mol) in methylene chloride. The resultant mixture is stirred 20 minutes and concentrated in vacuo. The resultant residue is purified by flash column chromatography using silica gel and 10:1 methylene chloride/ethyl acetate to give the title product as a white solid (0.240 g, 83.6%, mp 260-262° C.) which is identified by NMR and IR spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-8d02f5f8d67a4a30be6f339666371ef0
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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