Hydrochloric Acid → N,N'-Didodecyldithiooxamide

HRID 893263Notes

Reaction equation

[NH2:1][C:2]([C:4]([NH2:6])=[S:5])=[S:3].N[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:14](N)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].Cl>CO>[CH2:14]([NH:1][C:2]([C:4]([NH:6][CH2:12][CH2:13][CH2:8][CH2:9][CH2:10][CH2:11][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:8])=[S:5])=[S:3])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 35 °C

Procedure

Into a 100 ml round-bottomed flask, equipped with a magnetic stirrer and heating bath, were placed 2.4 g (0.02 mol) of dithiooxamide, 1.8 g (0.02 mol) of aniline, and 40 ml of methanol. The solution was stirred and heated at 35° C. for 30 minutes. The reactive amine, dodecylamine (3.7 g, 0.02 mol), was then added, and the solution was stirred for an additional 3 hours at 35° C. The crude reaction mixture was cooled to 25° C., and the acidity was adjusted to a pH of about 2 by the addition of 37% aqueous HCl. The mixture was filtered, washed with a small amount of methanol, and dried to afford 1.5 g of N,N'-didodecyldithiooxamide. Water (40 ml) was added to the filtrate with stirring, which was continued for 10 minutes. The precipitate was collected by filtration and washed with a minimum amount of a 50:50 mixture of water and methanol. The product was dried to afford 3.2 g (55%) of N-dodecyldithiooxamide.

Workup

customInto a 100 ml round-bottomed flask, equipped with a magnetic stirrer
temperatureheating bath
stirringthe solution was stirred for an additional 3 hours at 35° C
customThe crude reaction mixture
temperaturewas cooled to 25° C.
filtrationThe mixture was filtered
washwashed with a small amount of methanol
customdried

Sources & evidence

ORD record: ord-3b096bd027734698bacf53f20ccbd683
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05124308

Reaction notes

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