Thionyl Chloride → HCID 178438090, compound

HRID 1165412

Reaction equation

HRID 1165412 reaction equation
[OH:1][N:2]=[C:3]([NH2:16])[CH:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)[CH3:5].Cl.NO.[O-]CC.[Na+].[O:24]1C=NN[S:25]1=O.S(Cl)(Cl)=O.C(=N)(N)CC>>[CH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:6]=1[CH:4]([C:3]1[NH:16][S:25](=[O:24])[O:1][N:2]=1)[CH3:5]

Participants

7

Reactant 6

HCID 24386Thionyl ChlorideHCID 415117Propionamidine hydrochlorideHCID 443297Hydroxyamine hydrochlorideHCID 2723922Sodium ethoxideHCID 22315334HCID 22315334, compoundHCID 53747220HCID 53747220, compound

Product 1

HCID 178438090HCID 178438090, compound

Procedure

The monomethyl compound (5.07 g) was converted to the N'-hydroxy-2-(naphthalen-2-yl)propanimidamide following the procedure of Example 1, with hydroxylamine hydrochloride and sodium ethoxide at reflux for three days. The product (4.18 g) was converted to the oxathiadiazole-2-oxide following the procedure of Example 1. The addition of thionyl chloride to the propanimidamide was performed at 0° C. over a thirty minute period. The crude product was purified by flash chromatography through a silica gel column employing dichloromethane, 0.5% ethyl acetate/dichloromethane, 1% ethyl acetate and 2% ethyl acetate serial elution solvents. The product is a light yellow oil.

Workup

  1. waitwas performed at 0° C. over a thirty minute period
  2. customThe crude product was purified by flash chromatography through a silica gel column

Sources & evidence

ORD record
ord-5fecb679a9c849cda2bb8de44c7ea071
Source dataset
uspto-grants-1990_03
Patent number
US04910019

Linked notes

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