Hydrochloric Acid → HCID 5162979, compound

HRID 838918Notes

Reaction equation

HRID 838918 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[C:7]([NH2:11])([CH3:10])([CH3:9])[CH3:8].[ClH:12].Cl[O-].[Na+]>O>[Cl:12][CH:3]([C:2]([CH3:1])=[O:6])[C:4]([NH:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 12661DiketeneHCID 23665760Sodium Hypochlorite

Product 1

HCID 5162979HCID 5162979, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Diketene (42 g, 0.5 mol) was mixed with ca. 200 ml of ice and water in a 2 l., 3-neck flask. A solution of t-butylamine (37.5 g, 0.5 mol) in water (150 ml) was added gradually with stirring and more ice was added as needed to keep the reaction at or below 20°. The solution was stirred for 20 minutes after completing the addition, acidified with concentrated HCl (400 ml), and cooled to 10° with an ice/acetone bath. Aqueous sodium hypochlorite ("Chlorox", 750 ml, 0.5 mol) was then added dropwise with rapid mechanical stirring. The product was filtered out, washed with water and air-dried for several hours to give 78.5 g (81.8%) of colorless solid.

Workup

  1. additionmore ice was added
  2. customthe reaction at or below 20°
  3. stirringThe solution was stirred for 20 minutes
  4. additionthe addition
  5. temperaturecooled to 10° with an ice/acetone bath
  6. filtrationThe product was filtered out
  7. washwashed with water
  8. customair-dried for several hours

Sources & evidence

ORD record
ord-46f6b4efa7ae4618a0926cb3c3447b99
Source dataset
uspto-grants-1978_06
Patent number
US04093654

Reaction notes

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