Thionyl Chloride → Hydrochloric Acid

HRID 1971248Notes

Reaction equation

HRID 1971248 reaction equation
[C:1]12([CH2:11][NH:12][C:13]([C:15]3[N:20]4[CH:21]=[C:22]([CH2:24]O)[N:23]=[C:19]4[CH:18]=[CH:17][CH:16]=3)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(Cl)([Cl:28])=O>>[C:1]12([CH2:11][NH:12][C:13]([C:15]3[N:20]4[CH:21]=[C:22]([CH2:24][Cl:28])[N:23]=[C:19]4[CH:18]=[CH:17][CH:16]=3)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[ClH:28]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 25269402HCID 25269402, compound

Product 2

HCID 313Hydrochloric AcidHCID 59451927HCID 59451927, compound

Procedure

N-(Adamantan-1-ylmethyl)-2-(hydroxymethyl)imidazo[1,2-a]pyridine-5-carboxamide (4.4 g, 12.96 mmol) is treated with 10 mL of thionyl chloride at RT for 1 h. The excess thionyl chloride is removed in vacuo to give the title compound as its HCl salt.

Workup

  1. customThe excess thionyl chloride is removed in vacuo

Sources & evidence

ORD record
ord-250994f04497433c88d4d4e29803475f
Source dataset
uspto-grants-2013_04
Patent number
US08431593B2

Reaction notes

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