Hydroxylamine → HCID 58121110, compound

HRID 1186700Notes

Reaction equation

HRID 1186700 reaction equation
[C:1]1([C:7]2[S:8][C:9]([C:18]([O:20]C)=O)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:22][OH:23].[OH-].[K+]>CO.C1COCC1>[OH:23][NH:22][C:18]([C:9]1[S:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:11][C:10]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:20]

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 58121052HCID 58121052, compound

Product 1

HCID 58121110HCID 58121110, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 100 mL round-bottomed flask was charged with methyl 2,4-diphenylthiazole-5-carboxylate 73 (420 mg, 1.422 mmol) in MeOH (2.844 ml) and THF (2.84 ml) and the solution was cooled down to 0° C. Then a 50% aqueous solution of hydroxylamine (4697 mg, 71.1 mmol) and 4M potassium hydroxide solution (0.427 ml, 1.706 mmol) were added and the reaction mixture was allowed to warm up to rt while stirring for 18 h. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with fresh EtOAc and the combined organic layers were washed with 1M HCl, sat NaHCO3, and brine, dried over MgSO4, filtered and concentrated. The resulting solid was triturated (Et2O) to afford the title compound 74 (0.303 g, 72% yield). 1H NMR: (DMSO-d6) d(ppm) 1H, 11.29 (s, 1H), 9.44 (s, 1H), 8.03 (dd, J=6.3, 2.7 Hz, 2H), 7.84 (d, J=7.0 Hz, 2H), 7.56-7.55 (m, 3H), 7.50-7.43 (m, 3H). LRMS (ESI): (calc.) 296.34 (found) 297.1 (MH)+

Workup

  1. temperatureto warm up to rt
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with fresh EtOAc
  4. washthe combined organic layers were washed with 1M HCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting solid was triturated (Et2O)

Sources & evidence

ORD record
ord-1c9493bfb2884362ae5e27331d9fea02
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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