Trifluoroborane-methyl sulfide → HCID 23653658, compound

HRID 1785507Notes

Reaction equation

HRID 1785507 reaction equation
CSC.B(F)(F)F.[CH2:8]([O:10][C:11]([C:13]1[S:17][C:16]([N:18]2[C:22]3[CH:23]=[C:24]([O:29]C)[C:25]([O:27]C)=[CH:26][C:21]=3[N:20]=[CH:19]2)=[N:15][C:14]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:12])[CH3:9]>C(Cl)Cl>[CH2:8]([O:10][C:11]([C:13]1[S:17][C:16]([N:18]2[C:22]3[CH:23]=[C:24]([OH:29])[C:25]([OH:27])=[CH:26][C:21]=3[N:20]=[CH:19]2)=[N:15][C:14]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 11137191Trifluoroborane-methyl sulfideHCID 24886662HCID 24886662, compound

Product 1

HCID 23653658HCID 23653658, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trifluoride dimethylsulfide (4.1 ml, 39 mmol) was added in multiportions over 5 hrs. to a suspension of 2-(5,6-Dimethoxybenzoimidazol-1-yl)-4-phenylthiazole-5-carboxylic acid ethyl ester (2.04 g, 4.99 mmol) in methylene chloride at RT. The mixture was stirred for an additional 40 mins. Ice water was added. Methylene chloride was removed, the residue was filtered, the solid was washed with water and a small amount of methanol, and then dried in air to give the product (1.72 g, yield 90%). 1H-NMR (DMSO-D6) 8.72 (s, 1H); 8.78-8.88 (m, 2H); 7.64 (s, 1H); 7.42-7.51 (m, 3H); 7.08 (s, 1H); 4.22 (q, 2H), 1.22 (t, 3H). MS M/z 382 (M+1)

Workup

  1. customMethylene chloride was removed
  2. filtrationthe residue was filtered
  3. washthe solid was washed with water
  4. dry with materiala small amount of methanol, and then dried in air

Sources & evidence

ORD record
ord-ccc8952ed6af4a2db53bf5335c8373ae
Source dataset
uspto-grants-2009_03
Patent number
US07504513B2

Reaction notes

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