Triethylamine → 3-(Methanesulfonyl)-2-(nitromethylidene)-1,3-thiazinane

HRID 1153715Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[N+:6]([CH:9]=[C:10]1[NH:15][CH2:14][CH2:13][CH2:12][S:11]1)([O-:8])=[O:7].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([N:15]1[CH2:14][CH2:13][CH2:12][S:11][C:10]1=[CH:9][N+:6]([O-:8])=[O:7])(=[O:4])=[O:3]

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of 20 g of methanesulfonyl chloride in 150 ml of methylene chloride was added drop-by-drop over a 55 minute period to a stirred mixture of 20 g of 2-(nitromethylene)-tetrahydro-2H-1,3-thiazine and 40 ml of triethylamine in 150 ml of methylene chloride, at -30° C., in a nitrogen atmosphere. The resulting mixture was stirred for 30 minutes at -30° C., and then washed with 2% hydrochloric acid. The aqueous phase was washed twice with methylene chloride. The resulting organic phases were combined, dried (Na2SO4), concentrated to about 50 ml, cooled to 0° C., and filtered. The crystalline solid was triturated with cold methylene chloride, to give N-(methylsulfonyl)-2-(nitromethylene)-tetrahydro-2H-1,3-thiazine (1A), as a crystalline solid, m.p.: 144-145° C. (with decomposition).

Workup

washwashed with 2% hydrochloric acid
washThe aqueous phase was washed twice with methylene chloride
dry with materialdried (Na2SO4)
concentrationconcentrated to about 50 ml
temperaturecooled to 0° C.
filtrationfiltered
customThe crystalline solid was triturated with cold methylene chloride

Sources & evidence

ORD record: ord-e3082018f1b846d8a6b9865dd156a11d
Source dataset: uspto-grants-1984_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04486427

Reaction notes

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