2-Amino-N-isopropylacetamide → HCID 59511750, compound

HRID 1157436Notes

Reaction equation

HRID 1157436 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH:6]([CH3:8])[CH3:7])=[O:4].[OH:9][C:10]1[CH:21]=[CH:20][C:13]2[NH:14]C(=O)[O:16][C:17](=O)[C:12]=2[CH:11]=1>C(#N)C.ClCCl>[NH2:14][C:13]1[CH:20]=[CH:21][C:10]([OH:9])=[CH:11][C:12]=1[C:17]([NH:1][CH2:2][C:3](=[O:4])[NH:5][CH:6]([CH3:8])[CH3:7])=[O:16]

Participants

5

Reactant 2

HCID 5338492-Amino-N-isopropylacetamideHCID 27593156-hydroxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 59511750HCID 59511750, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-N-isopropylacetamide (INTERMEDIATE I.1) (4.77 g, 41.1 mmol) in acetonitrile (50 mL) was added 6-hydroxy-1H-benzo[d][1,3]oxazine-2,4-dione (6.13 g, 34.2 mmol). The mixture was stirred for 16 h at room temperature during which time a very thick precipitate formed. The mixture was diluted with dichloromethane (100 mL) and the solid collected by filtration and washed with dichloromethane (2×20 mL) to afford 2-amino-5-hydroxy-N-(isopropylcarbamoylmethyl)benzamide (INTERMEDIATE II.1) (6.75 g, 32.0 mmol, 78%).

Workup

  1. customformed
  2. filtrationthe solid collected by filtration
  3. washwashed with dichloromethane (2×20 mL)

Sources & evidence

ORD record
ord-f7378be7695f4ae89605fa8f14191602
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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