Sodium Bicarbonate → HCID 54455874, compound

HRID 429485Notes

Reaction equation

HRID 429485 reaction equation
[CH3:1][NH:2][CH2:3][C@H:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:5][CH:6]=[CH2:7].CC(C)=O.O.C(=O)(O)[O-].[Na+].[CH3:24][O:25][C:26]1[CH:34]=[CH:33][C:32]([N:35]2[CH:39]=[N:38][N:37]=[N:36]2)=[CH:31][C:27]=1[C:28](Cl)=[O:29]>C(OCC)(=O)C>[CH3:1][N:2]([CH2:3][C@H:4]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:5][CH:6]=[CH2:7])[C:28](=[O:29])[C:27]1[CH:31]=[C:32]([N:35]2[CH:39]=[N:38][N:37]=[N:36]2)[CH:33]=[CH:34][C:26]=1[O:25][CH3:24]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 153920222-Methoxy-5-(1H-tetrazol-1-yl)benzoyl ChlorideHCID 18366337Propan-2-one--water (1/1)HCID 53688463(S)-N-methyl-(2-phenylpent-4-enyl)amine

Product 1

HCID 54455874HCID 54455874, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine (S)-N-methyl-(2-phenylpent-4-enyl)amine (1.93 g, 11.0 mmol), acetone/water (4/1, 125 mL), and sodium bicarbonate (3.0 g, 35.5 mmol). Cool in an ice bath with vigorous stirring. Add portionwise, 2-methoxy-5-(1H-tetrazol-1-yl)benzoyl chloride (2.86 g, 11.8 mmol). After the addition is complete, warm to ambient temperature. After 1.5 hours, evaporate in vacuo to remove most of the acetone. Extract the evaporated reaction mixture with ethyl acetate. Extract the organic layer with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give (S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(1H-tetrazol-1-yl)benzamide: Rf=0.35 (silica gel, ethyl acetate).

Workup

  1. temperatureCool in an ice bath with vigorous stirring
  2. additionAdd portionwise
  3. additionAfter the addition
  4. customevaporate in vacuo
  5. customto remove most of the acetone
  6. extractionExtract
  7. customthe evaporated reaction mixture with ethyl acetate
  8. extractionExtract the organic layer with a saturated aqueous sodium bicarbonate solution
  9. dry with materialDry the organic layer over MgSO4
  10. filtrationfilter
  11. customevaporate in vacuo
  12. customto give a residue

Sources & evidence

ORD record
ord-e1127994fa7a4edeb832f2d89359648f
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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