Ethanol → HCID 13345267, compound

HRID 462296Notes

Reaction equation

HRID 462296 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 ad 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 ad
  6. customThe residual solid is recrystallized from cyclohexane
  7. customto give 1.58 g

Sources & evidence

ORD record
ord-8f4f3029647446aba0cb98950f52314b
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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