Potassium Carbonate → HCID 14372421, compound

HRID 2058404Notes

Reaction equation

[CH2:1]([O:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]([O:14][C:15](Cl)=[O:16])[CH:11]=[CH:12][CH:13]=1)=[O:6])[C:2]#[CH:3].[CH2:18]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=1)[CH:19]([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>C(OC(=O)C)C.O>[CH2:1]([O:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]([O:14][C:15](=[O:16])[N:22]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[CH:11]=[CH:12][CH:13]=1)=[O:6])[C:2]#[CH:3]

Participants

Conditions

Temperature: 15 °C

Procedure

A solution of 25.4 g (0.1 mol) of chloroformic acid-3-(2-propinyl-oxycarbonylamino)-phenylester in 100 ml acetic acid ethylester is added within a period of 20 minutes to a solution of 16.3 g (0.1 mol) of N-isobutyl-p-toluidine in 50 ml acetic acid ethylester. Simultaneously a solution of 13.8 g (0.1 mol) of potassium carbonate in 50 ml water is added dropwise while stirring and cooling to 15° C. temperature. Thereafter, the solution is further stirred at 15° C. for 30 minutes. The organic phase is then separated and washed at 0° C. with dilute sodium hydroxide, dilute hydrochloric acid and water. After drying on magnesium sulfate the mass is concentrated at a reduced pressure. It is then recrystallized from acetic acid ethylester/pentane.

Workup

stirringThereafter, the solution is further stirred at 15° C. for 30 minutes
customThe organic phase is then separated
washwashed at 0° C. with dilute sodium hydroxide, dilute hydrochloric acid and water
customAfter drying on magnesium sulfate the mass
concentrationis concentrated at a reduced pressure
customIt is then recrystallized from acetic acid ethylester/pentane

Sources & evidence

ORD record: ord-8d2f4336a4984572b07767c5ba0daeb1
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04317674

Reaction notes

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