Formic Acid → HCID 15485565, compound

HRID 367247Notes

Reaction equation

HRID 367247 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=O)[CH3:2].[CH:8]([OH:10])=O.Cl.Cl.[NH2:13][C:14]1[CH:19]=[CH:18]C=C[CH:15]=1.[CH2:20]([N:22](CC)[CH2:23][CH3:24])[CH3:21]>CN(C=O)C>[N:22]1([CH2:2][CH2:1][O:4][C:5]2[CH:6]=[CH:15][C:14]([NH:13][CH:8]=[O:10])=[CH:19][CH:18]=2)[CH2:23][CH2:24][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 21479679HCID 21479679, compound

Product 1

HCID 15485565HCID 15485565, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Acetic anhydride (9.2 g, 90 mmol) was cooled under a nitrogen atmosphere to 0° C. and treated dropwise with formic acid (4.9 g, 108 mmol). This mixture was stirred at 0° C. for 30 min then warmed to 60° C. for 2 h. The reaction mixture was cooled to room temperature and treated with a mixture of the above aniline dihydrochloride (10.1 g, 36 mmol) and triethylamine (18.3 g, 181 mmol) in 150 mL dry DMF. The reaction was stirred at ambient temperature for 2 h then concentrated under vacuum to a solid which was mixed with saturated NaHCO3 and brine. This was concentrated to a solid and rinsed with THF. The rinses were concentrated to 5.6 g of an oil (24 mmol, 66%).

Workup

  1. temperaturethen warmed to 60° C. for 2 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. stirringThe reaction was stirred at ambient temperature for 2 h
  4. concentrationthen concentrated under vacuum to a solid which
  5. additionwas mixed with saturated NaHCO3 and brine
  6. concentrationThis was concentrated to a solid
  7. washrinsed with THF

Sources & evidence

ORD record
ord-6831057f527248e8a03600c8a26ef787
Source dataset
uspto-grants-2000_10
Patent number
US06133262

Reaction notes

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