Triethylamine → HCID 136415275, compound

HRID 1959396Notes

Reaction equation

HRID 1959396 reaction equation
[NH2:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.Cl.[NH2:12][OH:13].C(N(CC)CC)C>CO>[NH2:1][C:2]1[C:3](/[C:9](=[N:12]\[OH:13])/[NH2:10])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 110526113-Amino-6-bromopyrazine-2-carbonitrile

Product 1

HCID 136415275HCID 136415275, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-amino-6-bromo-pyrazine-2-carbonitrile (4.5958 g, 23.09 mmol) was dissolved in MeOH (91.92 mL), cooled to 0° C. and treated with hydroxylamine hydrochloride (1.605 g, 23.09 mmol) and triethylamine (2.336 g, 3.218 mL, 23.09 mmol). The reaction was allowed to warm to ambient temperature, stirred for 48 hours and then evaporated to dryness. Methanol (a minimum amount) was added, the mixture sonicated, filtered and washed with MeOH to give the product as a brown solid 5.27 g, 98% Yield). 1H NMR (400.0 MHz, DMSO) d 5.88 (s, 2H), 7.64 (br s, 2H), 8.14 (s, 1H) and 10.38 (s, 1H) ppm; MS (ES+) 233.75

Workup

  1. temperatureto warm to ambient temperature
  2. customevaporated to dryness
  3. additionMethanol (a minimum amount) was added
  4. customthe mixture sonicated
  5. filtrationfiltered
  6. washwashed with MeOH

Sources & evidence

ORD record
ord-18d51cfd67b341dfb5cf01bd649bbf6b
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

Loading…