Ethyl Acetate → Ethyl (2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-carbamate

HRID 403163Notes

Reaction equation

HRID 403163 reaction equation
[NH2:1][C:2]1[C:17]([F:18])=[CH:16][C:5]2[O:6][C:7]([F:15])([F:14])[C:8](=[O:13])[N:9]([CH2:10][C:11]#[CH:12])[C:4]=2[CH:3]=1.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21].CCOC(C)=O.CCCCCCC>C1(C)C=CC=CC=1>[F:15][C:7]1([F:14])[C:8](=[O:13])[N:9]([CH2:10][C:11]#[CH:12])[C:4]2[CH:3]=[C:2]([NH:1][C:20](=[O:21])[O:22][CH2:23][CH3:24])[C:17]([F:18])=[CH:16][C:5]=2[O:6]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 10928Ethyl chloroformateHCID 866695376-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 87293554Ethyl (2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-carbamateYield 40.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2Hbenzo[b][1,4]oxazin-3(4H)-one (2.0 g, 7.8 mmol) and ethyl chloroformate (1.14 g, 10.5 mmol) in dry toluene was heated to reflux for 2 hours. The mixture was evaporated to dryness to obtain a brown solid. Column chromatography (silica, EtOAc: heptane, 1:3) gave the product (1.04 g), which was used without further purification in the next step 1.8a.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThe mixture was evaporated to dryness
  4. customto obtain a brown solid

Sources & evidence

ORD record
ord-86a3181ba630441ca478e629cd4bb60b
Source dataset
uspto-grants-2014_06
Patent number
US08748348B2

Reaction notes

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