Butyl isocyanate → HCID 12790745, compound

HRID 1733315Notes

Reaction equation

HRID 1733315 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH2:7][C@@H:8]([C:10]([OH:12])=O)[NH2:9])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:15]([N:19]=[C:20]=[O:21])[CH2:16][CH2:17][CH3:18]>>[CH2:15]([N:19]1[C:10](=[O:12])[CH:8]([CH2:7][C:5]2[S:6][C:2]([CH3:1])=[CH:3][CH:4]=2)[NH:9][C:20]1=[O:21])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 8110Butyl isocyanateHCID 14798Sodium HydroxideHCID 22813574HCID 22813574, compound

Product 1

HCID 12790745HCID 12790745, compound

Conditions

Temperature
0 °C

Procedure

DL-β-(5-Methylthiophen-2-yl)alanine (4.1 g; 0.022 mole) was dissolved in 2 N sodium hydroxide solution (11 ml; 0.022 mole), cooled to 0° C. and n-butyl-isocyanate (3.75 ml; 0.033 mole) added gradually maintaining the temperature at 0° C. for 2 hours. The mixture was allowed to come to room temperature and stirred overnight. The mixture was filtered (solid discarded) and the filtrate washed with ether. The washed filtrate was acidified with concentrated hydrochloric acid (11 ml) and heated on a steam bath for 1 hour. After cooling to room temperature the resultant solid was separated by filtration, water washed and dried. Recrystallisation from ethyl acetate gave the title compound. Yield 4.2 g (72%), m.p. 107° C.

Workup

  1. temperaturemaintaining the temperature at 0° C. for 2 hours
  2. customto come to room temperature
  3. filtrationThe mixture was filtered (solid discarded)
  4. washthe filtrate washed with ether
  5. temperatureheated on a steam bath for 1 hour
  6. temperatureAfter cooling to room temperature the resultant solid
  7. customwas separated by filtration, water
  8. washwashed
  9. customdried
  10. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-a4c3c838629741789834c6ab08a164dd
Source dataset
uspto-grants-1980_12
Patent number
US04241073

Reaction notes

Loading…