Sodium Hydroxide → HCID 86656488, compound

HRID 75773Notes

Reaction equation

HRID 75773 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[S:25][C:26]4[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=4[N:28]=3)=[CH:19][CH:18]=2)=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:5])C.[OH-].[Na+]>C1COCC1>[F:33][C:31]1[CH:30]=[CH:29][C:27]2[N:28]=[C:24]([NH:23][C:20]3[CH:21]=[CH:22][C:17]([C:7]4[C:6]([C:4]([OH:5])=[O:3])=[C:10]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[O:9][N:8]=4)=[CH:18][CH:19]=3)[S:25][C:26]=2[CH:32]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866564893-[4-(6-Fluoro-benzothiazol-2-ylamino)-phenyl]-5-phenyl-isoxazole-4-carboxylic acid ethyl ester

Product 1

HCID 86656488HCID 86656488, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound 3-[4-(6-fluoro-benzothiazol-2-ylamino)-phenyl]-5-phenyl-isoxazole-4-carboxylic acid ethyl ester (10.9 g; 23.7 mmol) was dissolved in 100 ml THF by heating at reflux to get a clear solution. To the solution, 1N NaOH (47.4 ml; 44.7 mmol) was added and the reaction mixture was stirred for 2 h. The solvent was removed. The residue was taken up in water and acidified with 2N HCl to pH 2. The solid was filtered and dried to provide 8 g of the title compound in 78.2% yield. 1H NMR (DMSO-d6) δ: 7.18 (m, 1H), 7.54-7.59 (m, 3H), 7.62-7.69 (m 3H), 7.76 (2×d, 1H), 7.84-7.92 (m, 4H), 10.76 (s, 1H); Mass (ES+), 432 (M++1).

Workup

  1. temperatureby heating
  2. temperatureat reflux
  3. customto get a clear solution
  4. customThe solvent was removed
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-3d8bc3405053411197a8dcce377ac7c3
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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