Triethylamine → HCID 15392143, compound

HRID 266453Notes

Reaction equation

HRID 266453 reaction equation
[SH:1][C:2]1[S:6][C:5]([S:7][CH2:8][N:9]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[S:10]2(=[O:12])=[O:11])=[N:4][N:3]=1.Cl.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25]Cl.C(N(CC)CC)C.C(OCC)(=O)C>CN(C=O)C>[CH3:22][N:23]([CH2:24][CH2:25][S:1][C:2]1[S:6][C:5]([S:7][CH2:8][N:9]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[S:10]2(=[O:12])=[O:11])=[N:4][N:3]=1)[CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 178515057HCID 178515057, compound

Product 1

HCID 15392143HCID 15392143, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following a procedure similar to that described in Example 33A above, 1.72 g (0.005 mol) of 2-(5-mercapto-1,3,4-thiadiazol-2-ylthiomethyl)saccharin was reacted with 1.44 g (0.01 mol) of 2-dimethylaminoethyl chloride hydrochloride in 10 ml of DMF in the presence of 1.72 g (0.017 mol) of triethylamine to give 1.2 g (58%) of 2-(5-[2-(N,N-dimethylamino)ethylthio]-1,3,4-thiadiazol-2-ylthiomethyl)saccharin, mp 90.5°-91.5° C. (from ethyl acetate).

Sources & evidence

ORD record
ord-8ef693afef06497fac9289b932528aba
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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