Acetic Acid → HCID 23039052, compound

HRID 1708985Notes

Reaction equation

HRID 1708985 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:4][CH:3]=1.[CH2:17]([N:20]=[C:21]=[O:22])[CH2:18][CH3:19].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:17]([NH:20][C:21]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:4][CH:3]=1)=[O:22])[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 61033Propyl isocyanateHCID 23039044HCID 23039044, compound

Product 1

HCID 23039052HCID 23039052, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2 g of 6-hydroxy-N,N-diethyl-1-indan-methylamine and 1.5 g of propylisocyanate were refluxed in 25 ml of dry toluene for 16 hours. The reaction mixture was poured into 100 ml of 0.1M acetic acid, and the organic phase was separated. The water phase was made alkaline with dil. NH4OH and extracted with 2×50 ml diethyl ether. The combined organic phases were dried (MgSO4) and the solvent evaporated. The residue was purified by column chromatography yielding 1.1 g of the title compound as an oil.

Workup

  1. customthe organic phase was separated
  2. extractionextracted with 2×50 ml diethyl ether
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. customthe solvent evaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-52392f9058d5470a9f5c10dd06157dc6
Source dataset
uspto-grants-1990_08
Patent number
US04946863

Reaction notes

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