Thionyl Chloride → HCID 59691698, compound

HRID 898546Notes

Reaction equation

HRID 898546 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29]O)=[CH:25][CH:24]=3)=[O:21])=[N:16][CH:17]=2)=[CH:8][CH:7]=1>ClCCl>[Cl:3][CH2:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:20](=[O:21])/[CH:19]=[CH:18]/[C:15]2[CH:14]=[CH:13][C:12]([C:9]3[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=3)=[CH:17][N:16]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 68878277HCID 68878277, compound

Product 1

HCID 59691698HCID 59691698, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 μL (0.680 mmol) thionyl chloride was added to a suspension of 0.190 g (0.520 mmol) (E)-3-[5-(4-chloro-phenyl)-pyridin-2-yl]-N-(4-hydroxymethyl-phenyl)-acrylamide (Z38a) in 20 mL dichloromethane and the mixture was stirred for 2 h at RT . Another 50 μL thionyl chloride were added and the mixture was again stirred for 3 h. The solvent was concentrated by evaporation i. vac., the residue taken up twice in toluene and concentrated by evaporation i. vac. The crude product was obtained as the HCl salt and used in the next reaction step without any further purification.

Workup

  1. stirringthe mixture was again stirred for 3 h
  2. concentrationThe solvent was concentrated by evaporation i
  3. concentrationconcentrated by evaporation i

Sources & evidence

ORD record
ord-f1c504c4c63b48698f97e4661e02142c
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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