Ammonia → HCID 3602273, compound

HRID 1395185Notes

Reaction equation

HRID 1395185 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH3:7].[H-].CCOCC.[H][H].[CH2:16]([CH:24]1[CH2:26][CH:25]1[C:27]([O:29]CC)=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].S(=O)(=O)(O)O>CCOCC>[CH2:16]([CH:24]1[CH2:26][CH:25]1[C:27]([NH2:7])=[O:29])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

8

Reactant 6

HCID 222Ammonia3×HCID 1118Sulfuric AcidHCID 12389515HCID 12389515, compoundHCID 21226445Aluminium lithium hydrideHCID 86736976HCID 86736976, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 3602273HCID 3602273, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
30 °C

Procedure

4 g of lithium aluminum hydride was mixed with 300 ml of dry ether under a nitrogen blanket. Gaseous ammonia was liquefied by a dry ice condenser and the liquefied ammonia was dripped over a period of one hour onto the hydride/ether mixture until no further evolution of hydrogen was observed (7 g of ammonia used). 22.6 g of 1 was added drop-by-drop over a period of one hour and the resulting solution was stirred for 3 hours at 30° C., then poured into a mixture of 500 ml of 5% sulfuric acid and 200 g of ice. The ether layer was separated and the aqueous layer was extracted with ether. The ether layer and extracts were combined and the ether was evaporated. The residue was recrystallized from hot hexane, then from cold methanol, to give 4, as a solid, mp: 109°-110° C.

Workup

  1. customThe ether layer was separated
  2. extractionthe aqueous layer was extracted with ether
  3. customthe ether was evaporated
  4. customThe residue was recrystallized from hot hexane
  5. customfrom cold methanol, to give 4

Sources & evidence

ORD record
ord-05fc8cf50a134b99abf8d99457f04ed7
Source dataset
uspto-grants-1980_05
Patent number
US04202902

Reaction notes

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