Sodium Hydroxide → HCID 10355566, compound

HRID 2114054Notes

Reaction equation

HRID 2114054 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[C:13]3[C:12]([C:24]3[CH:28]=[CH:27][O:26][CH:25]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO.O>[O:26]1[CH:27]=[CH:28][C:24]([C:12]2[C:13]3[C:14](=[N:15][CH:16]=[C:17]([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=3)[NH:10][CH:11]=2)=[CH:25]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59812182HCID 59812182, compound

Product 1

HCID 10355566HCID 10355566, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 33 (28.3 mg, 0.0696 mmol) in EtOH (1.4 mL), was added 10% aqueous NaOH (0.67 mL), and the reaction mixture refluxed (oil bath 110° C.) for 0.5 h. The mixture was diluted with water (1.4 mL), and stirred for an additional 0.5 h at r.t. The precipitate was filtered off, washed with water, and dried under high vacuum to afford 34 as tan solid (15.8 mg, 85%); 1H NMR (400 MHz; CDCl3) δ 6.72 (dd, J=1.8, 0.8 Hz, 1H), 7.14 (dd, J=5.1, 3.6 Hz, 1H), 7.32-7.36 (m, 2H), 7.48 (d, J=2.5 Hz, 1H), 7.55 (t, J=1.7 Hz, 1H), 7.82 (m, 1H), 8.23 (dd, J=2.0, 0.4 Hz, 1H), 8.65 (d, J=2.0 Hz, 1H), 9.67 (bs, 1H).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-425bbd25f2f745828e7555707f40c865
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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