proline dl-form → HCID 12767213, compound

HRID 904136Notes

Reaction equation

HRID 904136 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([OH:5])=O.[OH-].[Na+].[CH2:11]([N:15]=[C:16]=[O:17])[CH2:12][CH2:13][CH3:14]>O>[CH2:11]([N:15]1[C:3](=[O:5])[CH:2]2[CH2:6][CH2:7][CH2:8][N:1]2[C:16]1=[O:17])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 614proline dl-formHCID 8110Butyl isocyanateHCID 14798Sodium Hydroxide

Product 1

HCID 12767213HCID 12767213, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

DL-Proline (2.5 g 0.0217 mole) was dissolved in water (20 ml) containing 2 N NaOH (10.9 ml, 0.0219 equiv) cooled to 0° C. and n-butyl isocyanate (3.27 g 0.33 mole) added dropwise to the stirred solution during 2 hours. The mixture was left at room-temperature overnight, filtered and washed with ether. The aqueous solution was acidified with concentrated hydrochloric acid (30 ml) and heated on the steam-bath for 30 minutes, cooled and continuously extracted with ether for 2 hours. Removal of the solvent gave a clear oil which was distilled under reduced pressure in a Kugelrohr apparatus to yield the product as a colourless oil, b.p. 90° C. at 0.02 mm. Yield 3.5 g=83%.

Workup

  1. filtrationfiltered
  2. washwashed with ether
  3. temperatureheated on the steam-bath for 30 minutes
  4. temperaturecooled
  5. extractioncontinuously extracted with ether for 2 hours
  6. customRemoval of the solvent
  7. customgave a clear oil which
  8. distillationwas distilled under reduced pressure in a Kugelrohr apparatus

Sources & evidence

ORD record
ord-dbd9756afa2a44f9b01f7d9cc214954c
Source dataset
uspto-grants-1980_10
Patent number
US04230709

Reaction notes

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