Ethylamine → HCID 62648753, compound

HRID 1041373Notes

Reaction equation

HRID 1041373 reaction equation
[F:1][C:2]1[C:7]2[NH:8]C(=O)O[C:11](=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:14]([NH2:16])[CH3:15]>O1CCCC1>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=1[C:11]([NH:16][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 105353938-Fluoroisatoic anhydride

Product 1

HCID 62648753HCID 62648753, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8-Fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (10.0 g, 55.2 mmol) was dissolved in tetrahydrofuran (200 mL, 2000 mmol) at 0° C. 2.0 M Ethylamine in tetrahydrofuran (41 mL) was added and the reaction was stirred for 2 hours. The reaction was concentrated under reduced pressure and azeotroped with toluene (50 mL). Ethyl ether (200 mL) was added and the precipitate (the acid byproduct formed by hydrolysis) was removed by filtration. The filtrate was concentrated under reduced pressure and the product was purified by silica gel chromatography using a gradient of 0-60% EtOAc/hex as the eluting solvent to obtain 2-amino-N-ethyl-3-fluoro-benzamide as a pale yellow solid (9.02 g, 90%). m.p.=60° C.; LCMS (m/e) 183 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 7.11 (d, 1H, J=8.0 Hz), 7.09-7.02 (m, 1H), 6.62-6.54 (m, 1H), 6.05 (bs, 1H), 5.61 (bs, 2H), 3.52-3.43 (m, 2H), 1.26 (t, 3H, J=6.6 Hz).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customazeotroped with toluene (50 mL)
  3. additionEthyl ether (200 mL) was added
  4. customthe precipitate (the acid byproduct formed by hydrolysis)
  5. customwas removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fedee3fc8bb7403183388b15f55bb7ca
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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