Hydroxylamine → HCID 89655910, compound

HRID 1477511Notes

Reaction equation

HRID 1477511 reaction equation
[C:1]([C:3]([NH:6][C:7]([C:9]1[O:10][C:11]([CH3:14])=[N:12][N:13]=1)=[O:8])([CH3:5])[CH3:4])#[N:2].[NH2:15][OH:16].CCCCCCC>C(O)(C)C>[NH2:2]/[C:1](=[N:15]\[OH:16])/[C:3]([NH:6][C:7]([C:9]1[O:10][C:11]([CH3:14])=[N:12][N:13]=1)=[O:8])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 8900HeptaneHCID 71623011HCID 71623011, compound

Product 1

HCID 89655910HCID 89655910, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
52.5 °C

Procedure

N-(2-cyanopropan-2-yl)-5-methyl-1,3,4-oxadiazole-2-carboxamide (II) (185 gms) was suspended in isopropyl alcohol (462 ml), heated to 50 to 55° C. Aqueous hydroxylamine (IIIa; 76 ml) was added and the reaction mixture stirred for 30 minutes at 60° C. After completion, reaction mass was cooled between 0 and 5° C. and heptane (462 ml) was added to the reaction mass. The resultant slurry was filtered, washed with heptane (185 ml) and the wet cake was dried to give N-[(1Z)-1-amino-1-(hydroxyimino)-2-methylpropan-2-yl]-5-methyl-1,3,4-oxadiazole-2-carboxamide (IVa).

Workup

  1. customAfter completion, reaction mass
  2. temperaturewas cooled between 0 and 5° C.
  3. filtrationThe resultant slurry was filtered
  4. washwashed with heptane (185 ml)
  5. customthe wet cake was dried

Sources & evidence

ORD record
ord-04354564b396491f9be8942f951b8ed5
Source dataset
uspto-grants-2016_08
Patent number
US09403809B2

Reaction notes

Loading…