Boron tribromide → HCID 59267961, compound

HRID 1809419Notes

Reaction equation

HRID 1809419 reaction equation
C([O:8][CH2:9][C:10]([C:13]1[S:17][C:16]([NH2:18])=[N:15][N:14]=1)([CH3:12])[CH3:11])C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:18][C:16]1[S:17][C:13]([C:10]([CH3:12])([CH3:11])[CH2:9][OH:8])=[N:14][N:15]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59267860HCID 59267860, compound

Product 1

HCID 59267961HCID 59267961, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(2-benzyloxy-1,1-dimethyl-ethyl)-1,3,4-thiadiazol-2-ylamine (15.0 g, 57.0 mmol) in DCM (100 mL), boron tribromide (1N in DCM, 15.0 mL, 162.0 mmol) is added slowly at 0° C. The reaction mixture is warmed up to room temperature and stirred for 3 h. After cooling the reaction mixture to 0° C., ice water is added. The two phases are separated and the pH of the water phase is adjusted to ˜13 with NaOH and extracted with n-BuOH. The organic layer is washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford 10.0 g of 2-(5-amino-1,3,4-thiadiazol-2-yl)-2-methyl-propan-1-ol as a brown solid; m/z 174 [M+H].

Workup

  1. temperatureAfter cooling the reaction mixture to 0° C.
  2. customThe two phases are separated
  3. extractionextracted with n-BuOH
  4. washThe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed930ca8fdf14c62abe6672bc9f0e096
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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