Triethylamine → HCID 18700293, compound
Reaction equation
ClC(OCC(C)C)=O.[CH2:9]1[CH2:21][O:20][C:11]2([CH2:16][CH2:15][CH:14]([C:17]([O-:19])=O)[CH2:13][CH2:12]2)[O:10]1.[Na+].C(N(CC)CC)C.Cl.[CH2:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][NH2:41])=[CH:36][CH:35]=1)[CH3:32]>O1CCCC1.O>[CH2:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([NH:40][NH:41][C:17]([CH:14]2[CH2:13][CH2:12][C:11]3([O:10][CH2:9][CH2:21][O:20]3)[CH2:16][CH2:15]2)=[O:19])=[CH:36][CH:35]=1)[CH3:32]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
At -40° C., 1.65 ml of isobutyl chloroformate are added to a mixture of 2.63 g of sodium 4,4-ethylenedioxycyclohexanoate in 20 ml of tetrahydrofuran followed by 1.8 ml of triethylamine. The reaction mixture is stirred for 2 hours at 0° C., then at -20° C., 2.4 g of 4-ethoxyphenylhydrazine hydrochloride are added; the reaction mixture is stirred for 2 hours at 0° C. then 100 ml of water are added and it is extracted with ethyl acetate. The organic phases are washed successively with water, with a solution of potassium bisulfate (pH=2), with a saturated potassium carbonate solution, dried over magnesium sulfate and evaporated off. The expected product is obtained after crystallisation from diethyl ether; M.p.=158° C.
Workup
- stirringthe reaction mixture is stirred for 2 hours at 0° C.
- extractionit is extracted with ethyl acetate
- washThe organic phases are washed successively with water, with a solution of potassium bisulfate (pH=2), with a saturated potassium carbonate solution
- dry with materialdried over magnesium sulfate
- customevaporated off
Sources & evidence
- ORD record
- ord-1d1079b9e4024387b1b01701b6149839
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06090818
Reaction notes
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