Diisopropylamine → HCID 18999574, compound

HRID 274125Notes

Reaction equation

HRID 274125 reaction equation
[CH:1](NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH3:13][C:14]1([CH3:21])[C:16]([CH3:18])([CH3:17])[CH:15]1[C:19]#[N:20].[O:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>CCCCCC.CN1CCN(C)C1=O>[OH:22][CH2:26][CH2:25][C:24]1[CH:11]=[CH:10][C:9]([CH2:1][C:15]2([C:19]#[N:20])[C:16]([CH3:18])([CH3:17])[C:14]2([CH3:21])[CH3:13])=[CH:8][CH:23]=1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 1283302980799-19-5HCID 178418339Butyllithium

Product 1

HCID 18999574HCID 18999574, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 8058HexaneSolvent

Procedure

Obtained by operating as in example 87a, from 19.7 g (195 mmoles) of diisopropylamine, 122 ml (195 mmoles) of a 1.6M solution of n-butyllithium in hexane, 45 ml of 1,3-dimethylimidazolidin-2-one, 21.8 g of 2,2,3,3-tetramethylcyclopropanecarbonitrile (prepared according to patent FR 2,479,192), 51.9 g (180.5 mmoles) of the compound prepared in example 26a in 295 ml tetrahydrofuran. After distillation, there is obtained 20 g (yield=44.0%) of a thick yellow oil. b.p.0.8 =185°-205° C.

Workup

  1. customObtained
  2. distillationAfter distillation

Sources & evidence

ORD record
ord-f00311c7e55e43e5bee4ceaff97473d0
Source dataset
uspto-grants-1995_02
Patent number
US05387709

Reaction notes

Loading…