6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one → HCID 67331922, compound

HRID 527958Notes

Reaction equation

HRID 527958 reaction equation
[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[CH2:12][O:11]1)([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=2[CH:26]=1>CCO.O>[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][CH2:7][CH2:8][CH2:9][C@@H:10]([OH:11])[CH2:12][NH:15][C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=2[CH:26]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27636816-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 11085223HCID 11085223, compound

Product 1

HCID 67331922HCID 67331922, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of (R)-tert-butyl-dimethyl-(3-oxiranyl-propoxy)-silane (13 g, 60 mmol; prepared according to Org. Lett. (2005), 7, 3997) and 6-amino-4H-benzo[1,4]oxazin-3-one (9.9 g) in EtOH/H2O (9:1, 325 mL) was heated at reflux overnight. The volatiles were removed under reduced pressure and the residue purified by CC (Hept/EA 1:1) to give the desired intermediate as a brown oil (8.9 g, 39% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe volatiles were removed under reduced pressure
  4. customthe residue purified by CC (Hept/EA 1:1)

Sources & evidence

ORD record
ord-a237a2786c37415c940823cc75e41eac
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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