tert-Butanol → HCID 53732321, compound

HRID 1779427Notes

Reaction equation

HRID 1779427 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.[C:25]1([C:31]([C:33]2[S:37]C(C(O)=O)=C[CH:34]=2)=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[C:25]1([C:31]([C:33]2[S:37][C:6]([NH:3][C:4](=[O:15])[O:45][C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:7][CH:34]=2)=[O:32])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 1082345879505-01-4

Product 1

HCID 53732321HCID 53732321, compound

Procedure

Triethylamine (0.72 ml, 5.2 mmol) and diphenylphosphoryl azide (1.1 ml, 5.1 mmol) are added to 5-(phenylcarbonyl)-thiophene-2-carboxylic acid (0.99 g, 4.3 mmol) in 40 ml of absolute tert-butanol. The reaction mixture is boiled under reflux for 5 hours. The solvent is distilled off. The residue is taken up in ethyl acetate and washed with water. The organic phase is dried over magnesium sulfate and filtered and the solvent is distilled off. The solid which remains is purified by flash chromatography (eluent: 25% v/v ethyl acetate in petroleum ether (40/60)).

Workup

  1. temperatureunder reflux for 5 hours
  2. distillationThe solvent is distilled off
  3. washwashed with water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. distillationthe solvent is distilled off
  7. customThe solid which remains is purified by flash chromatography (eluent: 25% v/v ethyl acetate in petroleum ether (40/60))

Sources & evidence

ORD record
ord-cdc8c483fd7d41c2b52630c82cafd347
Source dataset
uspto-grants-1997_05
Patent number
US05627198

Reaction notes

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