Ammonium Hydroxide → HCID 21704177, compound

HRID 1595203Notes

Reaction equation

HRID 1595203 reaction equation
C[C:2]1[CH:26]=[CH:25][C:5]([C:6]([O:8][CH:9]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=O)=S)=[CH:4][CH:3]=1.CC1C=CC([C:32](OC(C2C=CC(F)=CC=2)C(C2C=CN=CC=2)=O)=[S:33])=CC=1.C([O-])(=O)C.[NH4+:57].[NH4+].[OH-]>C(O)(=O)C.O>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[N:57]=[C:6]([C:5]3[CH:25]=[CH:26][C:2]([S:33][CH3:32])=[CH:3][CH:4]=3)[O:8][C:9]=2[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 17912636HCID 17912636, compoundHCID 54029238HCID 54029238, compound

Product 1

HCID 21704177HCID 21704177, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution containing a mixture of 2-(4-fluorophenyl)-1-(4-pyridyl)-2-oxoethyl 4-methylthiobenzoate and 1-(4-fluorophenyl)-2-(4-pyridyl)-2-oxoethyl 4 methylthiobenzoate (1.0 g, 2.62 mmol) in glacial acetic acid (50 mL) was added ammonium acetate (2.0 g, 26.2 mmol). The resulting mixture was heated at reflux for 1.5 h, then allowed to cool. The mixture was poured into H2O, neutralized with conc. NH4OH and extracted with CH2Cl2. The combined organic extracts were washed with sat'd NaCl and dried over MgSO4. Purification by column chromatography, eluting with 5:1 to 1:1 Hex/EtOAc afforded the title compound (77.6 mg) as a yellow solid: ESMS (m/z): 363.0 (M++H).

Workup

  1. additionTo a solution containing
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for 1.5 h
  4. temperatureto cool
  5. extractionextracted with CH2Cl2
  6. washThe combined organic extracts were washed with sat'd NaCl
  7. dry with materialdried over MgSO4
  8. customPurification by column chromatography
  9. washeluting with 5:1 to 1:1 Hex/EtOAc

Sources & evidence

ORD record
ord-7205511cc57e4c74988ebe8e7b6915a6
Source dataset
uspto-grants-2001_09
Patent number
US06288062B1

Reaction notes

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