Cyanogen Bromide → 2-(5-Amino-1,3,4-oxadiazol-2-yl)-1,1,1-trifluorobutan-2-ol

HRID 1988208Notes

Reaction equation

HRID 1988208 reaction equation
[OH:1][C:2]([C:9]([F:12])([F:11])[F:10])([CH2:7][CH3:8])[C:3]([NH:5][NH2:6])=[O:4].Br[C:14]#[N:15]>O>[NH2:15][C:14]1[O:4][C:3]([C:2]([OH:1])([CH2:7][CH3:8])[C:9]([F:10])([F:11])[F:12])=[N:5][N:6]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 57729255Butanoic acid, 2-hydroxy-2-(trifluoromethyl)-, hydrazide

Product 1

HCID 469421982-(5-Amino-1,3,4-oxadiazol-2-yl)-1,1,1-trifluorobutan-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To hydrazide (34.07 g, 183 mmol) of step 2 in 275 mL of water was added KHCO3 (18.33 g, 183 mmol) followed by BrCN (19.39 g, 183 mmol) portionwise. After 3 h, the solid was filtered, washed with cold water and dried to afford the title compound. Additional compound could be recovered from the aqueous phase by extraction (ether-hexane, 1:1). 1H NMR (400 MHz, acetone-d6): δ 6.54 (s, 2H), 6.01 (s, 1H), 2.22 (m, 1H), 2.08 (m, 1H) and 0.99 (m, 3H).

Workup

  1. filtrationthe solid was filtered
  2. washwashed with cold water
  3. customdried

Sources & evidence

ORD record
ord-b951095335714f0e81ea9d4706ed5ad4
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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