Hydrochloric Acid → HCID 178437587, compound

HRID 555944Notes

Reaction equation

HRID 555944 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]([NH:11][NH:12][C:13]([NH:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH3:25])[CH:20]=[CH:19]3)=[S:14])=O)[C:6]([O:26][CH3:27])=[CH:5][C:4]=1[O:28][CH3:29])[CH3:2].[OH-].[Na+].Cl>>[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[N:15]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH3:25])[CH:20]=[CH:19]4)[C:13]([SH:14])=[N:12][N:11]=2)[C:6]([O:26][CH3:27])=[CH:5][C:4]=1[O:28][CH3:29])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86621683N[6-ethyl-3,5-dimethoxy-pyridine-2-carboxamidyl]-N'-(1-Methyl-1H-indol-5-yl)-thiourea

Product 1

HCID 178437587HCID 178437587, compound

Procedure

A flask was charged with N-[6-ethyl-3,5-dimethoxy-pyridine-2-carboxamidyl]-N′-(1-Methyl-1H-indol-5-yl)-thiourea (41 mg; 0.10 mmol), and one normal aqueous sodium hydroxide (2 mL), and the reaction was stirred at reflux under nitrogen for three hours. The reaction was then cooled, adjusted to pH=7 with one normal hydrochloric acid, and the precipitate was extracted with dichloromethane (2×6 mL). The organic layers were dried with sodium sulfate, and evaporated to give quantitative yield of 5-(6-Ethyl-3,5-dimethoxy-pyridin-2-yl)-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazole-3-thiol.

Workup

  1. temperatureat reflux under nitrogen for three hours
  2. temperatureThe reaction was then cooled
  3. extractionthe precipitate was extracted with dichloromethane (2×6 mL)
  4. dry with materialThe organic layers were dried with sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-5ac0d21b3d114c98b2aa837f95bfbda2
Source dataset
uspto-grants-2011_11
Patent number
US08053456B2

Reaction notes

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