Hydrochloric Acid → HCID 135843668, compound

HRID 48966Notes

Reaction equation

HRID 48966 reaction equation
C[O:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]1[C:12]2[CH:13]=[C:14]([N:17]3[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]3=[O:29])[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1.B(Cl)(Cl)Cl.Cl>C(Cl)Cl>[OH:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]1[C:12]2[CH:13]=[C:14]([N:17]3[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]3=[O:29])[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25135Boron TrichlorideHCID 20634218HCID 20634218, compound

Product 1

HCID 135843668HCID 135843668, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-[3-(3-methoxy-2-thienyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil(0.500 g, 1.14 mmol) and methylene chloride at −5° C. is added boron trichloride (1M in methylene chloride, 2.30 ml, 2.3 mmol) via syringe. The resultant mixture is stirred two hours at −5° C., warmed to room temperature, stirred overnight and poured into cold 10% hydrochloric acid. The mixture is extracted with methylene chloride. The organic layer is washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to an oil. The oil is crystallized in ether to afford the title compound as pale yellow-green crystals (0.350 g, 72.2%) which is characterized by NMR spectral analysis.

Workup

  1. extractionThe mixture is extracted with methylene chloride
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo to an oil
  5. customThe oil is crystallized in ether

Sources & evidence

ORD record
ord-03f803fbf3b44d4fba1d97ba2159325f
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

Loading…