Thionyl Chloride → HCID 19424196, compound

HRID 743160Notes

Reaction equation

[Cl:1][C:2]1[N:3]([CH3:14])[C:4]2[C:9]([C:10]=1[C:11]([OH:13])=O)=[CH:8][CH:7]=[CH:6][CH:5]=2.O=S(Cl)Cl.Cl.[CH3:20][O:21][C:22](=[O:25])[CH2:23][NH2:24]>>[C:22]([CH2:23][NH:24][C:11]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]([CH3:14])[C:2]=1[Cl:1])=[O:13])([O:21][CH3:20])=[O:25]

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 995221H-Indole-3-carboxylic acid, 2-chloro-1-methyl-

HCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 19424196HCID 19424196, compoundYield 78%

Procedure

Similar reaction of 2-chloro-1-methylindole-3-carboxylic acid [XXI] with SOCl2 and glycine methyl ester hydrochloride gave N-carbomethoxymethyl 2-chloro-1-methylindole-3-carboxamide [XXII: R6 =H, R7 -CH2COOMe] (78% yield); mp (CHCl3 /light petroleum) 102.5°-104° C.

Sources & evidence

ORD record: ord-3b042c98dcaf4b2ba7851e559e801c81
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05556874

Reaction notes

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