Methanol → HCID 69521578, compound

HRID 456594Notes

Reaction equation

HRID 456594 reaction equation
CSC.B.[N:5]1[S:9][N:8]=[C:7]2[CH:10]=[C:11]([CH2:14][C:15](O)=[O:16])[CH:12]=[CH:13][C:6]=12.CO>O1CCCC1.C(OCC)(=O)C>[N:5]1[S:9][N:8]=[C:7]2[CH:10]=[C:11]([CH2:14][CH2:15][OH:16])[CH:12]=[CH:13][C:6]=12

Participants

6

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 54776280HCID 54776280, compound

Product 1

HCID 69521578HCID 69521578, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

Borane methylsulfide (1.6 ml) was added dropwise to a cold solution (8–10° C.) of crude benzo[1,2,5]thiadiazol-5-yl-acetic acid (b) (2.8 g, 14 mmol) in tetrahydrofuran (20 ml). Stirring was continued for 1.25 hours while maintaining the temperature below 30° C. The mixture was cooled to 10° C. then methanol was added (1.4 ml) and the mixture was left 15 hours in the refrigerator. The mixture was diluted with ethyl acetate, washed with water then with a saturated aqueous solution of sodium hydrogencarbonate and again with water. The organic phase was separated, dried over magnesium sulfate and evaporated. The residue was triturated in pentane, collected by filtration and dried to give crude 2-benzo[1,2,5]thiadiazol-5-yl-ethanol (1.8 g, 71%).

Workup

  1. temperaturewhile maintaining the temperature below 30° C
  2. waitthe mixture was left 15 hours in the refrigerator
  3. washwashed with water
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was triturated in pentane
  8. filtrationcollected by filtration
  9. customdried

Sources & evidence

ORD record
ord-14468a5597064183908f0ddf0ea79279
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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