Water → 6-methoxy-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amine

HRID 1050713Notes

Reaction equation

HRID 1050713 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[S:21][C:22]([CH2:25][NH:26][CH2:27][CH3:28])=[CH:23][N:24]=1.O>CN(C)C=O>[CH3:12][O:11][C:4]1[N:3]=[C:2]([N:26]([CH2:25][C:22]2[S:21][C:20]([Cl:19])=[N:24][CH:23]=2)[CH2:27][CH3:28])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27950292-Chloro-6-methoxy-3-nitropyridineHCID 22450338N-((2-Chlorothiazol-5-yl)methyl)ethanamine

Product 1

HCID 716028016-methoxy-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amineYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.26 g 2-chloro-6-methoxy-3-nitropyridine and 10 mL N,N-dimethylformamide (DMF), and 2.00 g of potassium carbonate were added into a 100 mL single neck flask, under stirring at room temperature, 1.20 g of 2-chloro-5-ethylaminomethylthiazole, prepared according to the example 1, in 5.0 mL DMF were added dropwise. After that, the reaction solution was heated to 40-80° C. and then reacted for 3-6 hr. After cooling down, the resulting mixture was added to water (50 mL), then treated by the method according to the example 1 to obtain 1.27 g of 6-methoxy-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amine, as a golden yellow solid, having the content of 98.6%, a yield of 58.3%, and the structure was confirmed by GC-Mass and 1H NMR.

Workup

  1. additionwere added dropwise
  2. temperatureAfter that, the reaction solution was heated to 40-80° C.
  3. customreacted for 3-6 hr
  4. temperatureAfter cooling down
  5. additiontreated by the method

Sources & evidence

ORD record
ord-972621a476504162a99f3ca3ea2eeb65
Source dataset
uspto-grants-2016_07
Patent number
US09386769B2

Reaction notes

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