Triethylamine → HCID 18699971, compound

HRID 2288607Notes

Reaction equation

HRID 2288607 reaction equation
[N:1]1([CH2:8][C:9]2[S:10][C:11]([C:14]([NH:16][NH2:17])=O)=[CH:12][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:18]([N:20](CC)CC)[CH3:19].[ClH:25].C(=N)(OCC)C.[Cl-].[NH4+]>C(O)C>[ClH:25].[ClH:25].[CH3:19][C:18]1[NH:17][N:16]=[C:14]([C:11]2[S:10][C:9]([CH2:8][N:1]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:13][CH:12]=2)[N:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 55213626HCID 55213626, compound

Product 1

HCID 18699971HCID 18699971, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5 ml of ethanol solution containing 1.01 g (4.0 mmol) of 2-(hexahydro-1H-azepin-1-yl)methylthiophene-5-carboxylic acid hydrazide was added 2.8 ml (20 mmol) of triethylamine and 2.48 g (20 mmol) of ethyl acetoimidate hydrochloride, and the mixture was stirred at room temperature for 21 hours. Then, 1.2 g of ammonium chloride was added and the mixture was stirred at 80° C. for 4 hours. The reaction solution was concentrated, 28% aqueous ammonia and chloroform were added to the resulting residue, and then the resulting organic layer was separated and dried over anhydrous magnesium sulfate. The solvent was evaporated and the resulting residue was subjected to a silica gel column chromatography, which was eluted with chloroform-methanol (80:1) to give 814 mg of the title compound in its free form. By subjecting this compound to salt formation using 4 N HCl/ethyl acetate, 593 mg of the title compound was obtained.

Workup

  1. stirringthe mixture was stirred at 80° C. for 4 hours
  2. concentrationThe reaction solution was concentrated
  3. addition28% aqueous ammonia and chloroform were added to the resulting residue
  4. customthe resulting organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. washwas eluted with chloroform-methanol (80:1)

Sources & evidence

ORD record
ord-66a49c6b2f3b4c38a201c7d7e5034c65
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

Loading…