Hydrochloric Acid → HCID 20535090, compound

HRID 1156626Notes

Reaction equation

[NH2:1][C:2]1[N:7]2[O:8][C:9](=[O:11])[N:10]=[C:6]2[N:5]=[C:4]([N:12]([CH2:16][CH:17]=[CH2:18])[CH2:13][CH:14]=[CH2:15])[N:3]=1.[CH3:19][C:20]([CH3:25])=[CH:21][C:22](Cl)=[O:23].Cl>CN(C)C1C=CN=CC=1.O.C(Cl)Cl.C(N(CC)CC)C>[CH2:13]([N:12]([CH2:16][CH:17]=[CH2:18])[C:4]1[N:3]=[C:2]([NH:1][C:22](=[O:23])[CH:21]=[C:20]([CH3:25])[CH3:19])[N:7]2[O:8][C:9](=[O:11])[N:10]=[C:6]2[N:5]=1)[CH:14]=[CH2:15]

Participants

Conditions

Temperature: 5 °C

Procedure

15 g. of 7-amino-5-diallylamino-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-2-one are suspended in 300 ml. of methylene chloride, 30 ml. of triethylamine and 0.9 g. of 4-dimethylaminopyridine. 10.66 g. of 3,3-dimethylacrylyl chloride in 100 ml. of methylene chloride are added dropwise while stirring and cooling to about 5° C. The mixture is then stirred at 0° C. for 1 hour, treated with water and adjusted to pH 4 with 3-N hydrochloric acid. The two phases are separated and the aqueous phase is extracted with methylene chloride. The combined organic extracts are dried over magnesium sulfate and evaporated under reduced pressure. The residue is recrystallized from methylene chloride/diethyl ether, there being obtained pure N-{5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl}3-methylcrotonamide having a melting point of 165°-166° C.

Workup

stirringThe mixture is then stirred at 0° C. for 1 hour
customThe two phases are separated
extractionthe aqueous phase is extracted with methylene chloride
dry with materialThe combined organic extracts are dried over magnesium sulfate
customevaporated under reduced pressure
customThe residue is recrystallized from methylene chloride/diethyl ether, there

Sources & evidence

ORD record: ord-0baf0fc7c9bb42079ced58d90a386cb7
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04336380

Reaction notes

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