4-Chlorobenzyl mercaptan → HCID 44544510, compound

HRID 1019646Notes

Reaction equation

HRID 1019646 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]#[N:12].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][SH:21])=[CH:16][CH:15]=1>CN(C)C=O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][S:21][C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=2[C:11]#[N:12])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 804094-Chlorobenzyl mercaptanHCID 534332396-Chloro-5-cyanopyridine-2-carboxylic acid

Product 1

HCID 44544510HCID 44544510, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 6-chloro-5-cyanopicolinic acid (30 mg, 0.16 mmol), 4-chlorophenyl methanethiol (24 ul, 0.18 mmol), and CsCO3 (156 mg, 0.48 mmol) in dimethylformamide (2 ml) was heated for 16 hrs at 45° C. After removal of the solvent, the residue was treated with water (2 ml) and acidified with 1N—HCl to pH2. The precipitate was collected by filtration and dried under vacuum to afford 40 mg (82%) of the desired product 52. 1H NMR (600 MHz, DMSO-d6) δ 13.6 (br s, 1H), 8.46 (d, 1H, J=7.8 Hz), 8.15 (d, 1H, J=7.8 Hz), 7.55 (d, 2H, J=9 Hz), 7.47 (d, 2H, J=9 Hz). MS: m/z Calcd 304.8 Found MH+ 305.0

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was treated with water (2 ml)
  3. filtrationThe precipitate was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-f5f8aef3b9bf47068b107a45b94b8902
Source dataset
uspto-grants-2014_05
Patent number
US08716283B2

Reaction notes

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