Ammonia → HCID 66919891, compound

HRID 523875Notes

Reaction equation

HRID 523875 reaction equation
[NH3:1].Cl.[Cl:3][C:4]1[CH:22]=[CH:21][C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([C:16](Cl)=[O:17])[CH:13]=[CH:12][C:11]=2[C:19]#[N:20])=[CH:6][CH:5]=1>ClCCl>[Cl:3][C:4]1[CH:22]=[CH:21][C:7]([CH2:8][S:9][C:10]2[N:15]=[C:14]([C:16]([NH2:1])=[O:17])[CH:13]=[CH:12][C:11]=2[C:19]#[N:20])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86650826HCID 86650826, compound

Product 1

HCID 66919891HCID 66919891, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dry ammonia gas was bubbled through a solution of 6-(4-chlorobenzylthio)-5-cyanopicolinoyl chloride hydrochloride 81 (60 mg, 0.17 mmol) in dichloromethane (10 ml) for 5 min at 0° C. The mixture was stirred for 1 hr at ambient temperature and concentrated in vacuo. The crude product was purified by recrystallization in ether to afford 25 mg (48%) of the desired product 83. 1H NMR (600 MHz, DMSO-d6) δ 8.37 (d, 1H, J=7.8 Hz), 7.84 (d, 1H, J=8.4 Hz), 7.49-7.47 (m, 2H), 7.38-7.37 (m, 2H), 4.74 (s, 2H). MS: m/z Calcd 303.8 Found MH+ 304.0

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified by recrystallization in ether

Sources & evidence

ORD record
ord-ea9cda99d2254e2ea1728708844b797a
Source dataset
uspto-grants-2016_05
Patent number
US09340505B2

Reaction notes

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