4-Chlorobenzyl mercaptan → HCID 44544510, compound

HRID 523873Notes

Reaction equation

HRID 523873 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-bdc8347a903540749ed9fa46cd6adb10
Source dataset
uspto-grants-2016_05
Patent number
US09340505B2

Reaction notes

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