Sodium Hydroxide → 2-(2,6-Dichlorophenyl)thiazolo[5,4-c]pyridine

HRID 2366166Notes

Reaction equation

HRID 2366166 reaction equation
C(N(C(C)C)C([S:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][C:15](=O)[C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:23])=S)(C)C.[OH-].[Na+]>Cl>[Cl:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[C:15]1[S:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[N:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86668987HCID 86668987, compound

Product 1

HCID 668014812-(2,6-Dichlorophenyl)thiazolo[5,4-c]pyridineYield 77.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-(2,6-dichlorobenzamido)pyridin-3-yl diisopropylcarbamodithioate (50 mg, 0.11 mmol) in 5 M HCl (10 mL) was stirred at 100° C. for 4 hours. The pH of the mixture was adjusted to 7 by the addition of 2N sodium hydroxide solution and the aqueous phase extracted with EtOAc (3×100 mL). The combined organic extract was washed with water (2×50 mL) and brine (100 ml), dried over Na2SO4 and evaporated. The crude product was re-crystallized from EtOAc/DCM/petroleum ether (1:10:10) to give the product as a white solid (24 mg, 76% yield). 1H NMR (500 MHz, MeOH-d4): δ 9.30 (s, 1H), 8.60 (d, J=5.5 Hz, 1H), 8.03 (d, J=5.5 Hz, 1H), 7.54-7.50 (m, 3H). LCMS (Method A): RT=4.84 min, m/z: 281.0 [M+H+].

Workup

  1. extractionthe aqueous phase extracted with EtOAc (3×100 mL)
  2. extractionThe combined organic extract
  3. washwas washed with water (2×50 mL) and brine (100 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe crude product was re-crystallized from EtOAc/DCM/petroleum ether (1:10:10)

Sources & evidence

ORD record
ord-aec000bf4da84b08bfdecdfd63bb4c30
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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