Triethylamine → N-carbomethoxy-N'-isopropylsulfamyl-O-isopropyl-isourea

HRID 1447155Notes

Reaction equation

[CH:1]([NH:4][S:5](Cl)(=[O:7])=[O:6])([CH3:3])[CH3:2].[C:9]([NH:13][C:14](=[NH:19])[O:15][CH:16]([CH3:18])[CH3:17])([O:11][CH3:12])=[O:10].C(N(CC)CC)C>O1CCCC1>[C:9]([NH:13][C:14](=[N:19][S:5](=[O:7])(=[O:6])[NH:4][CH:1]([CH3:3])[CH3:2])[O:15][CH:16]([CH3:17])[CH3:18])([O:11][CH3:12])=[O:10]

Participants

Conditions

Temperature: 25 °C

Procedure

In the course of 25 minutes, 95 parts of isopropylaminosulfonyl chloride were stirred into a mixture of 96 parts of N-carbomethoxy-O-isopropylisourea and 73 parts of triethylamine in 700 parts of tetrahydrofuran at 10°-15° C. After then stirring for one hour at 25° C., the reaction mixture was extracted once with water and once with 0.5 N hydrochloric acid, dried and evaporated down under reduced pressure. This gave 130 parts of N-carbomethoxy-N'-isopropylsulfamyl-O-isopropyl-isourea, of melting point 62°-64° C. 33.7 parts of this product were cyclized with 17.6 parts of 50% strength by weight sodium hydroxide solution in 30 parts of water for 5 minutes at 55°-60° C. The mixture was extracted with ether and then acidified, and the product was filtered off, washed with water and dried, giving 22 parts of 6-isopropyl-3-isopropoxy-6H-1,2,4,6-thiatriazin-5-one,1,1-dioxide of melting point 164°-167° C.

Workup

extractionthe reaction mixture was extracted once with water and once with 0.5 N hydrochloric acid
customdried
customevaporated down under reduced pressure

Sources & evidence

ORD record: ord-96fd36b20f3d4ea093fbbaa376911c52
Source dataset: uspto-grants-1982_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04316015

Reaction notes

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