Dimethylformamide → HCID 178452974, compound

HRID 873785Notes

Reaction equation

HRID 873785 reaction equation
N[N:2]([CH:10]=[NH:11])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)=O.C(OCC)(=O)C.C[N:29](C)C=O>>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]1[N:29]=[C:10]([NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[NH:11][CH:13]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 383842-BromoacetamidopyridineHCID 86691067Tert-butyl amino(imino)methylcarbamate

Product 1

HCID 178452974HCID 178452974, compoundYield 27%

Procedure

tert-Butyl amino(imino)methylcarbamate (33.4 g; 210 mmol) was dissolved in N,N-dimethylformamide (300 mL), 2-bromo-1-pyridin-2-ylethanone (17.4 g; 87 mmol) was added thereto, and the mixture was stirred for 143 hours at room temperature. To the reaction solution, ethyl acetate (2.0 L) was added, and the mixture was washed with saturated aqueous sodium bicarbonate solution (three times). The organic layer was dried over anhydrous magnesium sulfate and then distilled under reduced pressure. The resulting oily substance was crystallized from diethyl ether and the resulting crystals were collected by filtration and dried to give 6.2 g of the title compound (yield 27%).

Workup

  1. washthe mixture was washed with saturated aqueous sodium bicarbonate solution (three times)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure
  4. customThe resulting oily substance was crystallized from diethyl ether
  5. filtrationthe resulting crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-d13e4d94324343368e40a00096b573d7
Source dataset
uspto-grants-2015_03
Patent number
US08975411B2

Reaction notes

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