Chloroform → N-hydroxy-4-pyridine-carboximidoyl chloride

HRID 653006Notes

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]=1

Participants

Reactant 2

HCID 6212Chloroform

HCID 127644-Pyridinecarbaldehyde oxime

Product 1

HCID 3014266N-hydroxy-4-pyridine-carboximidoyl chloride

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.l 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-fdd27ee55a92436a90e8c3bdb3aeb39c
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04675044

Reaction notes

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