Triethylamine → HCID 178505125, compound

HRID 2402238Notes

Reaction equation

HRID 2402238 reaction equation
[NH2:1][C:2]1[C:3]([C:7](Cl)=[N:8][OH:9])=[N:4][O:5][N:6]=1.Cl.Cl.[NH2:13][CH2:14][CH2:15][NH:16][S:17]([CH3:20])(=[O:19])=[O:18].C(N(CC)CC)C>C(O)C>[NH2:1][C:2]1[C:3]([C:7](=[N:8][OH:9])[NH:13][CH2:14][CH2:15][NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[N:4][O:5][N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4040027(Z)-4-amino-N-hydroxy-1,2,5-oxadiazole-3-carbonimidoyl chlorideHCID 86638021N-(2-Aminoethyl)methanesulfonamide dihydrochloride

Product 1

HCID 178505125HCID 178505125, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Amino-N-hydroxy-1,2,5-oxadiazole-3-carboximidoyl chloride (9.7 g, 60 mmol) was stirred in ethanol (460 mL) and N-(2-aminoethyl)methanesulfonamide dihydrochloride (19 g, 109 mmol) was added slowly in portions and the temperature rose to 25° C. After cooling back to 0° C., triethylamine (53 mL, 380 mmol) was added dropwise over 15 minutes and the reaction was stirred for an additional 15 minutes. The solution was washed with water (300 mL) and brine (300 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to give the desired product (16 g, 100%). LCMS calculated for C6H13N6O4S (M+H)+: m/z=265.1. 1H NMR (400 MHz, DMSO-d6): δ 10.16 (s, 1H), 9.07 (m, 1H), 7.18 (m, 1H), 6.37 (s, 2H), 3.36 (m, 2H), 3.15 (m, 2H), 2.87 (s, 3H).

Workup

  1. customrose to 25° C
  2. washThe solution was washed with water (300 mL) and brine (300 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0cb427ec318244e787ebea310cc6d2f2
Source dataset
uspto-grants-2014_08
Patent number
US08796319B2

Reaction notes

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