Sodium Hydroxide → HCID 21480750, compound

HRID 1490153Notes

Reaction equation

HRID 1490153 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[N:21](S(C(F)(F)F)(=O)=O)[S:22]([C:25]([F:28])([F:27])[F:26])(=[O:24])=[O:23].[OH-].[Na+]>C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[NH:21][S:22]([C:25]([F:26])([F:27])[F:28])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19073284HCID 19073284, compound

Product 1

HCID 21480750HCID 21480750, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-(naphth-2-yloxy)-4-nitrophenyl)-N,N-bis(trifluoromethanesulfonyl)amine (o.428 g, 0.79 mmol) in THF (10 mL) was added excess aqueous sodium hydroxide (2 mL, 10% aqueous NaOH). The resulting solution was stirred for 10 minutes at ambient temperature and quenched by adding excess 10% aqueous HCl. The two phased solution was partitioned between ethyl acetate and water. The organic layer was washed (2x, brine) dried (Na2 SO4), filtered and concentrated in vacuo. Recrystallization from ether/hexanes afforded the title compound. mp 117-120° C.; 1HNMR (300 MHz, CDCl3) δ 7.21(dd; J=9.3 Hz; 1H), 7.53 (d; J=2.5 Hz; 1H), 7.56-7.59 (m; 2H), 7.64 (d; J=2.5 Hz; 1H), 7.83 (d; J=9 Hz; 1H), 7.86-8.03 (m=3H); Anal. Calcd for C17H11N2O5 F3S: C, 49.52; H, 2.69; N, 6.79. Found: C, 49.52; H, 2.69; N, 6.75.

Workup

  1. customquenched
  2. additionby adding excess 10% aqueous HCl
  3. customThe two phased solution was partitioned between ethyl acetate and water
  4. washThe organic layer was washed (2x, brine)
  5. customdried (Na2 SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customRecrystallization from ether/hexanes

Sources & evidence

ORD record
ord-c032987e1b524ad6bc54db00716c018a
Source dataset
uspto-grants-1997_10
Patent number
US05681842

Reaction notes

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