Thionyl Chloride → HCID 68844582, compound

HRID 1984724Notes

Reaction equation

HRID 1984724 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[C:15]([S:20][CH:21]([NH:28][C:29](=[O:32])[CH2:30]O)[C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:35])=O>ClCCl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[C:15]([S:20][CH:21]([NH:28][C:29](=[O:32])[CH2:30][Cl:35])[C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67220046HCID 67220046, compound

Product 1

HCID 68844582HCID 68844582, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-tert-Butylphenyl)-2-(2-hydroxyacetylaminopyridin-4-ylmethylthio)pyridine-3-carboxamide (Compound No. 12-8, 250 mg, 0.55 mmol) was suspended in anhydrous dichloromethane (5.0 mL) under ice-cooling, and thionyl chloride (80 μL, 1.1 mmol) was added thereto. The mixture was stirred for 6 hours at room temperature, and the solvent was evaporated under reduced pressure. The resulting solid was filtered off with ethyl acetate and washed with diethyl ether to give 270 mg of the target compound quantitatively as a pale yellow solid.

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated under reduced pressure
  3. filtrationThe resulting solid was filtered off with ethyl acetate
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-75dba9613a03413093ee3c5908c24c03
Source dataset
uspto-grants-2009_06
Patent number
US07544703B2

Reaction notes

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