Ethylamine → 3-N-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-4-N-ethyl-1,1-dioxo-1,2,5-thiadiazole-3,4-diamine

HRID 1702348Notes

Reaction equation

HRID 1702348 reaction equation
COC1C(OC)=NS(=O)(=O)N=1.C(N)C.CO[C:17]1[C:21]([NH:22][CH2:23][CH3:24])=[N:20][S:19](=[O:26])(=[O:25])[N:18]=1.[CH3:27][N:28]([CH2:30][C:31]1[O:35][C:34]([CH2:36][S:37][CH2:38][CH2:39][NH2:40])=[CH:33][CH:32]=1)[CH3:29]>>[CH3:29][N:28]([CH2:30][C:31]1[O:35][C:34]([CH2:36][S:37][CH2:38][CH2:39][NH:40][C:17]2[C:21]([NH:22][CH2:23][CH3:24])=[N:20][S:19](=[O:26])(=[O:25])[N:18]=2)=[CH:33][CH:32]=1)[CH3:27]

Participants

5

Reactant 4

HCID 6341EthylamineHCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 122305383,4-Dimethoxy-1,2,5-thiadiazole 1,1-dioxideHCID 178463655N-ethyl-4-methoxy-1,1-dioxo-1,2,5-thiadiazol-3-amine

Product 1

HCID 1784636543-N-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-4-N-ethyl-1,1-dioxo-1,2,5-thiadiazole-3,4-diamine

Procedure

Reaction of a methanolic suspension of 3,4-dimethoxy-1,2,5-thiadiazole 1,1-dioxide with one equivalent of ethylamine and treatment of the resultant 3-methoxy-4-ethylamino-1,2,5-thiadiazole 1,1-dioxide with one equivalent of 2-[(5-dimethylaminomethyl-2-furyl)methylthio]ethylamine yields the title compound, which is identical to the product prepared in Example 12.

Sources & evidence

ORD record
ord-e258310e3d01406da1770338a5cbfffd
Source dataset
uspto-grants-1983_04
Patent number
US04380639

Reaction notes

Loading…