Ammonia → HCID 22666426, compound

HRID 1007889Notes

Reaction equation

HRID 1007889 reaction equation
[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]1[CH:20]=[CH:19][C:12]2[S:13][C:14]([C:16](O)=[O:17])=[CH:15][C:11]=2[CH:10]=1)[CH3:2].[NH3:23].C(OCC)(=O)C>O1CCCC1>[CH2:1]([N:3]([CH2:21][CH3:22])[CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]1[CH:20]=[CH:19][C:12]2[S:13][C:14]([C:16]([NH2:23])=[O:17])=[CH:15][C:11]=2[CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 22666517HCID 22666517, compound

Product 1

HCID 22666426HCID 22666426, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 30 mL of tetrahydrofuran is dissolved 2.18 g of 5-{2-[2-(diethylamino)ethoxy]ethyl}benzo[b]-thiophene-2-carboxylic acid, to which is added 1.98 g of N,N′-carbonyldiimidazole. The resulting mixture is stirred at ambient temperature for one hour. Then, 50 mL of 25% aqueous ammonia is added to the mixture and the resulting mixture is stirred at ambient temperature for one hour. Ethyl acetate is added to the mixture, the organic layer is separated, washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent:chloroform:methanol to chloroform:methanol:ammonia=5:1 to 100:10:1). Thus, 2.00 g of 5-{2-[2-(diethylamino)ethoxy]ethyl}benzo[b]-thiophene-2-carboxamide is obtained as a colorless crystalline product.

Workup

  1. stirringthe resulting mixture is stirred at ambient temperature for one hour
  2. customthe organic layer is separated
  3. washwashed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customthe residue is purified by column chromatography (eluent:chloroform:methanol to chloroform:methanol:ammonia=5:1 to 100:10:1)

Sources & evidence

ORD record
ord-4b60e3a85a694ae89a22d924c0b08bdc
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

Loading…