Ethanol → HCID 13345267, compound

HRID 1448556Notes

Reaction equation

HRID 1448556 reaction equation
[CH2:1]1[O:18][C:4]2([CH2:9][CH2:8][C:7](C(O)=O)([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1.C([N:21]([CH2:24]C)CC)C.C1C=CC(OP([O:38][C:39]2[CH:44]=CC=CC=2)(N=[N+]=[N-])=O)=CC=1.C([OH:47])C>>[CH2:2]1[O:3][C:4]2([CH2:5][CH2:6][C:7]([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)([NH:21][C:24]([O:38][CH2:39][CH3:44])=[O:47])[CH2:8][CH2:9]2)[O:18][CH2:1]1

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 12595554HCID 12595554, compound

Product 1

HCID 13345267HCID 13345267, compoundYield 51%

Procedure

To a solution of 2.68 g. (0.010 mole) of 4-carboxy-4-(2-thienyl)cyclohexanone ethylene ketal and 1.39 ml. triethylamine in 40 ml. ethanol there is added 2.75 g. diphenylphosphonic azide. Following 5 hours' heating at reflux the bulk of the solvent is removed in vacuum. The residue is dissolved in water and ether:benzene. The organic layer is washed in turn with water, ice cold 2.5 N hydrochloric acid, water, saturated sodium bicarbonate and brine and taken to dryness. The residual solid is recrystallized from cyclohexane to give 1.58 g. (51% yield) of 4-(2-thienyl)-4-ethoxycarbonylaminocyclohexanone ethylene ketal, m.p. 113°-117° C.

Workup

  1. temperature' heating
  2. temperatureat reflux the bulk of the solvent
  3. customis removed in vacuum
  4. dissolutionThe residue is dissolved in water
  5. washThe organic layer is washed in turn with water, ice cold 2.5 N hydrochloric acid, water, saturated sodium bicarbonate and brine
  6. customThe residual solid is recrystallized from cyclohexane
  7. customto give 1.58 g

Sources & evidence

ORD record
ord-4efde7655ed24072905726cf183d99aa
Source dataset
uspto-grants-1979_12
Patent number
US04180584

Reaction notes

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