Acetic Anhydride → Diisopropylethylamine

HRID 1721749Notes

Reaction equation

HRID 1721749 reaction equation
[C:1](OC(=O)C)(=O)C.C(O[C:13](=O)[CH2:14][CH3:15])(=O)CC.C([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])C.C1COCC1>C(OC(=O)C)C.C(COC)OC.C1(C)C=CC=CC=1>[CH:22]([N:19]([CH:14]([CH3:13])[CH3:15])[CH2:20][CH3:21])([CH3:23])[CH3:1]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31263Propionic anhydride

Product 1

HCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The amide acid VIIC is cyclized by treatment with a cyclizing agent such as acetic anhydride or propionic anhydride (employing a molar ratio of anhydride:VIIC of within the range of from about 7:1 to about 5:1) and amine base such as triethylamine or diisopropylethylamine, in the presence of an inert organic solvent such as THF, toluene, monoglyme or ethylacetate, at a temperature within the range of from about 70° to about 110° C., to form compound XXVIII.

Sources & evidence

ORD record
ord-02c0d93ef5da4e81962719d241f29889
Source dataset
uspto-grants-1996_04
Patent number
US05512690

Reaction notes

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