Triethylamine → N-(Cyanomethyl) 2-acetoxy 4-acetamino 5-chlorobenzamide

HRID 256335Notes

Reaction equation

C(N(CC)CC)C.Cl.[NH2:9][CH2:10][C:11]#[N:12].[C:13]([O:16][C:17]1[CH:25]=[C:24]([NH:26][C:27]([CH3:29])=[O:28])[C:23]([Cl:30])=[CH:22][C:18]=1[C:19](Cl)=[O:20])(=[O:15])[CH3:14]>C(Cl)(Cl)Cl>[C:11]([CH2:10][NH:9][C:19](=[O:20])[C:18]1[CH:22]=[C:23]([Cl:30])[C:24]([NH:26][C:27]([CH3:29])=[O:28])=[CH:25][C:17]=1[O:16][C:13](=[O:15])[CH3:14])#[N:12]

Participants

Conditions

Temperature: 5 °C

Procedure

104 g of triethylamine and 890 cc of chloroform were introduced into a 3 liter balloon flask provided with a sealed agitator, a reflux condenser and a thermometer. The solution obtained was cooled to 5° C. 51 g of amino acetonitrile hydrochloride was then gradually added, with the temperature being maintained at between 5° and 10° C. Thereafter over a period of 30 minutes and at a temperature of between 0° and 5° C., 143 g of 2-acetoxy 4-acetamino 5-chlorobenzoyl chloride in finely divided form was added. A dark-coloured solution resulted, which was agitated, first, for a period of 2 hours at 10° C. and, thereafter, for 2 hours at ambient temperature.

Workup

customprovided with a sealed agitator, a reflux condenser
customThe solution obtained
temperaturebeing maintained at between 5° and 10° C
customA dark-coloured solution resulted
waitfirst, for a period of 2 hours at 10° C.
waitfor 2 hours at ambient temperature

Sources & evidence

ORD record: ord-d48e83ed5b444f4c9689eca66cfc0423
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04703055

Reaction notes

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