Dimethyl Sulfide → HCID 9859873, compound

HRID 555811Notes

Reaction equation

HRID 555811 reaction equation
B(F)(F)F.CCOCC.CSC.[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[C:22]([C:24]1[CH:29]=[CH:28][C:27]([O:30]CC2C=CC=CC=2)=[CH:26][CH:25]=1)=[O:23]>C(Cl)Cl>[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[C:22]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)=[O:23]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 8000Boron trifluoride etherateHCID 59351412HCID 59351412, compound

Product 1

HCID 9859873HCID 9859873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 1 L round bottom flask was charged in a solution of boron trifluride diethyl etherate (101.2 g, 312 mmol) and dimethylsulfide (112 g, 809 mmol) in dry methylenedichloride (300 ml). Benzo[d]thiazol-2-yl(4-(benzyloxy)phenyl)methanone (30 g, 86.9 mmol) was added slowly to the mixture and the resulting solution was stirred at room temperature for 72 h. The reaction mixture was then quenched with water and diluted with CH2Cl2. The organic phase was washed with brine, dried (Na2SO4) and concentrated. The crude product was purified by silica gel column chromatography with hexane and ethyl acetate to give benzo[d]thiazol-2-yl(4-hydroxyphenyl)methanone. [M+H]=256.

Workup

  1. customThe reaction mixture was then quenched with water
  2. additiondiluted with CH2Cl2
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography with hexane and ethyl acetate

Sources & evidence

ORD record
ord-cd0904f7e6a44036b35dddf0adc1c6a1
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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