Chloroform → N-hydroxy-4-pyridine-carboximidoyl chloride
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[N:8][OH:9])=[CH:3][CH:2]=1.C(Cl)(Cl)[Cl:11]>>[OH:9][N:8]=[C:7]([Cl:11])[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1Participants
Procedure
4-Pyridinecarboxaldehyde oxime (30.6 g, 0.25 mol) was chlorinated in chloroform (350 ml) as described in Example 1 to produce N-hydroxy-4-pyridine-carboximidoyl chloride which was suspended in ether (500 ml) containing 2-chloroethanethiol (26.9 g, 0.25 mol). With ice bath cooling, triethylamine (5.1 g, 0.5 mol) was added dropwise. After the addition, water was made, the suspended solid, crude 2-chloroethyl N-hydroxy-4-pyridinecarboximidothioate was collected on a filter and dried. This crude ester was added to a solution of sodium ethoxide (from 5.75 g sodium in 500 ml ethanol), and the reaction mixture stirred for 4 hours. Water was added and the product was extracted with ether to give 5,6-dihydro-3-(4-pyridinyl)-1,4,2-oxathiazine, mp 80°-82° C., (found: C, 53.16; H, 4.56; N, 15.07. C8H8N2OS requires C, 53.33; H, 4.48; N, 15.55).
Sources & evidence
- ORD record
- ord-745b46e86de743059f05fa2396831600
- Source dataset
- uspto-grants-1986_02
- Patent number
- US04569690
Reaction notes
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