2,6-Dichlorobenzoyl chloride → HCID 86668987, compound

HRID 2366165Notes

Reaction equation

HRID 2366165 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4](Cl)=[O:5].[CH:12]([N:15]([CH:26]([CH3:28])[CH3:27])[C:16]([S:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[NH2:25])=[S:17])([CH3:14])[CH3:13]>C(Cl)Cl>[CH:26]([N:15]([CH:12]([CH3:14])[CH3:13])[C:16]([S:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[NH:25][C:4](=[O:5])[C:3]1[C:2]([Cl:1])=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:11])=[S:17])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 783922,6-Dichlorobenzoyl chlorideHCID 11437145Carbamodithioic acid, bis(1-methylethyl)-, 4-amino-3-pyridinyl ester

Product 1

HCID 86668987HCID 86668987, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 2,6-dichlorobenzoyl chloride (62 mg, 0.30 mmol) in DCM (4 mL) was slowly added to a cooled (0° C.) solution of 4-aminopyridin-3-yl diisopropylcarbamodithioate (100 mg, 0.37 mmol) in DCM (15 mL). The solution was stirred at 20° C. for 30 minutes. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluting with EtOAc/petroleum ether (1:4) to give the desired product as a yellow solid (20 mg, 15% yield). LCMS (ESI) m/z: 442.1 [M+H+].

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with EtOAc/petroleum ether (1:4)

Sources & evidence

ORD record
ord-0fbef040eed0496b8e770a068241cf95
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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