Thionyl Chloride → HCID 53863292, compound

HRID 1194187Notes

Reaction equation

[Na].[CH3:2][N:3]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[C:14]([C:15]([O-])=[O:16])=[CH:13][C:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:11][N:10]=2)[CH2:4]1.S(Cl)([Cl:26])=O>>[CH3:2][N:3]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[C:14]([C:15]([Cl:26])=[O:16])=[CH:13][C:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:11][N:10]=2)[CH2:4]1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 86741888HCID 86741888, compound

Product 1

HCID 53863292HCID 53863292, compound

Procedure

The crude salt: sodium-2-[(1-methyl-3-pyrrolidinyl)oxy]-5-phenyl-3-pyridinecarboxylate (96 g) prepared in Preparation 55 was mixed with about 400 ml of thionyl chloride and stirred at room temperature for 10 minutes. The unreacted thionyl chloride was evaporated off at 70° C. and the residue was azeotroped with toluene to give the title compound which was used to prepare 2-(2-chloroethyl)-2,3-dihydro-4-methyl-7-phenylpyrido[3,2-f]-1,4-oxazepin-5-(4H)-one midway in preparation of Intermediate 79.

Workup

customThe unreacted thionyl chloride was evaporated off at 70° C.
customthe residue was azeotroped with toluene

Sources & evidence

ORD record: ord-749715d7d0584cac9a8d630776a735bf
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04812565

Reaction notes

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