Tert-Butylamine → NSC55572

HRID 992752Notes

Reaction equation

HRID 992752 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[C:8]([NH2:12])([CH3:11])([CH3:10])[CH3:9]>C(#N)C>[C:8]([NH:12][C:1](=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 7923Maleic Anhydride

Product 1

HCID 5356375NSC55572Yield 72.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-7 °C

Procedure

To a 12L four necked round bottom flask with a mechanical stirrer, thermometer and an addition funnel, under nitrogen, was added 1072.6 grams of maleic anhydride (10.9 moles) and 6062 grams of acetonitrile. The mixture was stirred to dissolve the solids and cooled to −7° C. To this was added 800 grams of t-butylamine (10.9 moles) slowly at a rate such that the temperature remained below 0° C. (approximately 2.5 hour addition). Following the addition the mixture was stirred at −7° C. for one hour and overnight at room temperature. The solid was collected by filtration, washed with 500 mL of acetonitrile and dried to give 1355 grams of (Z)-4-(tert-butylamino)-4-oxo-2-butenoic acid as a white solid. 13-C NMR shows this to be 94.62 wt % (Z)-4-(tert-butylamino)-4-oxo-2-butenoic acid, and 5.38 wt % t-butylamine. This material was used without further purification for the next reaction.

Workup

  1. dissolutionto dissolve the solids
  2. customremained below 0° C.
  3. addition(approximately 2.5 hour addition)
  4. additionthe addition the mixture
  5. stirringwas stirred at −7° C. for one hour and overnight at room temperature
  6. filtrationThe solid was collected by filtration
  7. washwashed with 500 mL of acetonitrile
  8. customdried

Sources & evidence

ORD record
ord-12e2dec130db48f2ab89b3e466692259
Source dataset
uspto-grants-2002_10
Patent number
US06469199B1

Reaction notes

Loading…