Potassium Carbonate → HCID 178465655, compound

HRID 1191630Notes

Reaction equation

HRID 1191630 reaction equation
[CH3:1][N:2]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[NH2:3].Cl.[C:12](=[NH:17])(OCC)[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:7]([O:6][C:4]([N:2]([CH3:1])[NH:3][C:12](=[NH:17])[CH3:13])=[O:5])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 37482801-Boc-1-methylhydrazine

Product 1

HCID 178465655HCID 178465655, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 1-methylhydrazinecarboxylate (10.0 g, 68.4 mmol), ethyl acetimidate hydrochloride (42.1 g, 342 mmol), and potassium carbonate (94.4 g, 684 mmol) in DMF (150 mL) was heated at 105° C. for 5 hours. The contents were cooled to 0° C. before the precipitated material was collected by vacuum filtration and resuspended in H2O (100 mL). After 30 minutes of vigorous stirring, the remaining precipitate was collected and dried in a 45° C. vacuum oven overnight to yield the title compound as a white solid (7.56 g, 59.0%): mp 187-189° C.; 1H NMR (400 MHz, DMSO-d6) δ 6.28 (br s, 1H), 2.77 (s, 3H), 1.64 (s, 3H), 1.36 (s, 9H).

Workup

  1. filtrationwas collected by vacuum filtration
  2. customthe remaining precipitate was collected
  3. customdried in a 45° C. vacuum oven overnight

Sources & evidence

ORD record
ord-33dd3a4d6b66417d88a4fe8ec140d7d7
Source dataset
uspto-grants-2014_03
Patent number
US08680121B2

Reaction notes

Loading…