N-Methylethylenediamine → HCID 178509325, compound

HRID 2097966Notes

Reaction equation

HRID 2097966 reaction equation
[Br:1][C:2]1[C:6]2[C:7]3[N:8]([CH:11]=[N:12][N:13]=3)C=[N:10][C:5]=2[S:4][CH:3]=1.CNCCN>CO.[Cl-].[NH4+]>[Br:1][C:2]1[C:6]([C:7]2[NH:8][CH:11]=[N:12][N:13]=2)=[C:5]([NH2:10])[S:4][CH:3]=1

Participants

5

Reactant 2

HCID 8014N-MethylethylenediamineHCID 596366779-Bromothieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine

Product 1

HCID 178509325HCID 178509325, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

9-Bromothieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine (551 mg, 2.16 mmol) and N-methylethane-1,2-diamine (1 ml, 11.3 mmol) in methanol (20 ml) was placed into a preheated oil bath at 60° C. After stirring for 15 min, the solution was diluted with saturated ammonium chloride and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 525 mg (99% yield) of 4-bromo-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine as a brown solid. Method [8] retention time 2.25 min by HPLC (M+245 and 247).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-106778288eb14b6e81346b786b9bdff2
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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