Triethylamine → HCID 66954038, compound

HRID 2096983Notes

Reaction equation

HRID 2096983 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.ClC(Cl)(O[C:9](=[O:15])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[NH:24]([C:26]1[C:31]([I:32])=[CH:30][CH:29]=[CH:28][N:27]=1)[NH2:25]>ClCCl>[CH:1]1([NH:4][C:9]([NH:25][NH:24][C:26]2[C:31]([I:32])=[CH:30][CH:29]=[CH:28][N:27]=2)=[O:15])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 94429TriphosgeneHCID 53402765Pyridine, 2-hydrazinyl-3-iodo-

Product 1

HCID 66954038HCID 66954038, compoundYield 237.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

Cyclopropylamine (0.12 g, 2.2 mmol) in dichloromethane (3 mL) was added to a solution of triphosgene (0.22 g, 0.74 mmol) in dichloromethane (5 mL) at 0° C. under argon. Triethylamine (0.59 mL, 4.2 mmol) in dichloromethane (3 mL) was then added and the resulting mixture was stirred at room temperature for 2 hours and then cooled to 0° C. 2-Hydrazino-3-iodopyridine (preparation 26b, 0.50 g, 2.1 mmol) in dichloromethane (5 mL) was added and the resulting mixture was stirred at room temperature overnight. The solution was cooled to 0° C. and a solid precipitated. The solid was filtered, washed with diethyl ether and dried to yield the title compound (0.56 g, 83%) as a white solid.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. temperatureThe solution was cooled to 0° C.
  4. customa solid precipitated
  5. filtrationThe solid was filtered
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-61b52f27eefd4aadaca7ba8084f8aae4
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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