tert-Butanol → HCID 54493274, compound

HRID 1779431Notes

Reaction equation

HRID 1779431 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([S:31]([C:34]2[S:38]C(C(O)=O)=C[CH:35]=2)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:25]1([S:31]([C:34]2[S:38][C:6]([NH:3][C:4](=[O:15])[O:46][C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:7][CH:35]=2)(=[O:32])=[O:33])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2202575-(Benzenesulfonyl)thiophene-2-carboxylic acid

Product 1

HCID 54493274HCID 54493274, compound

Procedure

Triethylamine (0.62 ml, 4.4 mmol) and diphenylphosphoryl azide (0.97 ml, 4.5 mmol) are added to 5-(phenylsulfonyl)thiophene-2-carboxylic acid (1.00 g, 3.7 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 green-black oil which remains is purified by flash chromatography (eluent: 33% 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 green-black oil which remains is purified by flash chromatography (eluent: 33% v/v ethyl acetate in petroleum ether (40/60))

Sources & evidence

ORD record
ord-1a12e22b73b24525b9999861d79ae096
Source dataset
uspto-grants-1997_05
Patent number
US05627198

Reaction notes

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