O-Ethyl hydrazinecarbothioate → Hydrochloric Acid

HRID 1768544Notes

Reaction equation

HRID 1768544 reaction equation
[CH2:1]([N:3]=[C:4]([N:13]1[C:22]2[C:17](=[CH:18][C:19]([C:23](=O)[C:24]([Cl:27])([CH3:26])[CH3:25])=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH3:2].[NH:29]([C:31]([O:33]CC)=[S:32])[NH2:30]>C(#N)C>[CH2:1]([N:3]=[C:4]([N:13]1[C:22]2[C:17](=[CH:18][C:19]([C:23]3[C:24]([CH3:26])([CH3:25])[S:32][C:31](=[O:33])[NH:29][N:30]=3)=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[CH3:2].[ClH:27]

Participants

5

Reactant 2

HCID 12567113O-Ethyl hydrazinecarbothioateHCID 18948569HCID 18948569, compound

Product 2

HCID 313Hydrochloric AcidHCID 9889253HCID 9889253, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.7 g of 1-(N-ethyl-p-methoxybenzimidoyl)-6-(2-chloro-2-methylpropionyl)-1,2,3,4-tetrahydroquinoline in 40 ml of acetonitrile is treated with 1 equivalent of O-ethyl hydrazinothioformate and the mixture is boiled for 2 hours. After customary working up, 5-[1-(N-ethyl-p-methoxybenzimidoyl)-1,2,3,4-tetrahydroquinolin-6-yl]-6,6-dimethyl-3,6-dihydro-2H-1,3,4-thiadiazin-2-one, m.p. 244° (hydrochloride), is obtained.

Sources & evidence

ORD record
ord-b5061b30ef9943ee8e814b8f43b8ed48
Source dataset
uspto-grants-1995_01
Patent number
US05378702

Reaction notes

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