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

HRID 1988200Notes

Reaction equation

HRID 1988200 reaction equation
[CH2:1]([C:3]([OH:10])([CH2:8][CH3:9])[C:4](OC)=O)[CH3:2].[OH2:11].[NH2:12][NH2:13].Br[C:15]#[N:16]>O>[NH2:16][C:15]1[O:11][C:4]([C:3]([OH:10])([CH2:8][CH3:9])[CH2:1][CH3:2])=[N:13][N:12]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 24654Hydrazine hydrate (1:1)HCID 45037043Methyl 2-ethyl-2-hydroxybutanoate

Product 1

HCID 574378393-(5-Amino-1,3,4-oxadiazol-2-yl)pentan-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 2-ethyl-2-hydroxybutanoate (19.7 g, 134.7 mol) and hydrazine hydrate (14 mL) was heated to 130° C. for 4 h. The mixture was cooled to rt and excess reagent removed under vacuum to yield of the hydrazide. To this hydrazide and KHCO3 (13.8 g, 138 mmol) in 150 mL of water was added portionwise BrCN (13.8 g, 131 mmol). After 90 min of stirring, the white solid was filtered, washed with ether and dried to yield the title compound. 1H NMR (400 MHz, acetone-d6): δ 6.20 (bs, 2H), 4.25 (s, 1H), 1.85 (m, 4H), 0.88 (t, 6H).

Workup

  1. temperatureThe mixture was cooled to rt
  2. customexcess reagent removed under vacuum to yield of the hydrazide
  3. filtrationthe white solid was filtered
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-50f3d47aecef4d5daf2c5a09327fa2da
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

Loading…