Methyl iodide → HCID 23372624, compound

HRID 1862974Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[C:14]([CH3:18])[C:15]([CH3:17])=[CH:16][C:8]=3[NH:7][C:6]=2[N:19]=1.[H-].[Na+].[CH3:23]I>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]2[C:11](=[O:12])[N:10]([CH3:23])[C:9]3[CH:13]=[C:14]([CH3:18])[C:15]([CH3:17])=[CH:16][C:8]=3[NH:7][C:6]=2[N:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture consisting of 6.7 gm of 6,11-dihydro-2,4,8,9-tetramethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, 150 ml of dimethyl formamide and 1.4 gm of 50% sodium hydride in mineral oil was stirred at 50° C. in a nitrogen atmosphere for 30 minutes. Thereafter, a solution of 7.1 gm of methyl iodide in 30 ml of dimethyl formamide was added dropwise at room temperature. The resulting mixture was heated on an oil bath at 120° C. for 1 hour, and was then evaporated in vacuo. The residue was admixed with water, the aqueous mixture was made alkaline with ammonia, and it was then extracted with chloroform. After separation of the 2,4,6,8,9,11-hexamethyl compound which had simultaneously formed in a silica gel column, the product was recrystallized from petroleum ether (b.p. 100°-140° C.), yielding 63% of theory of the compound named in the heading, which had a melting point of 225°-227° C.

Workup

temperatureThe resulting mixture was heated on an oil bath at 120° C. for 1 hour
customwas then evaporated in vacuo
extractionwas then extracted with chloroform
customAfter separation of the 2,4,6,8,9,11-hexamethyl compound which
customhad simultaneously formed in a silica gel column
customthe product was recrystallized from petroleum ether (b.p. 100°-140° C.)
customyielding 63% of theory of the compound

Sources & evidence

ORD record: ord-8ce8c33497504101a415110f4d1d8d29
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04167570

Reaction notes

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