Triethylamine → HCID 178518903, compound

HRID 2288617Notes

Reaction equation

HRID 2288617 reaction equation
[N:1]1([CH2:8][C:9]2[S:10][C:11]([C:14]([NH:16][NH2:17])=[O:15])=[CH:12][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19].C(N(CC)CC)C>O1CCCC1.CN(C)C=O>[OH:19][C:18]1[O:15][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:16][N:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 55213626HCID 55213626, compound

Product 1

HCID 178518903HCID 178518903, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

760 mg (3.0 mmol) of 2-(hexahydro-1H-azepin-1-yl)methylthiophene-5-carboxylic acid hydrazide was dissolved in 30 ml of tetrahydrofuran and 3 ml of N,N-dimethylformamide, 583 mg (3.6 mmol) of 1,1'-carbonyldiimidazole and 0.84 ml (6.0 mmol) of triethylamine were added, and the mixture was heated under reflux for 3 hours. The reaction solution was concentrated, chloroform was added to the resulting residue, followed by washing with water and drying over anhydrous magnesium sulfate. The solvent was evaporated and the resulting residue was purified by a silica gel column chromatography to give 793 mg of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction solution was concentrated
  4. additionchloroform was added to the resulting residue
  5. washby washing with water
  6. dry with materialdrying over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-fc86c67959244edab285e035c22c069a
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

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