1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(2-Benzothienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

HRID 448762Notes

Reaction equation

HRID 448762 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]=[C:14]1[C:22]([NH:24][C:25]1([C:31]([OH:33])=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=O>C(Cl)Cl>[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:15]=[C:14]1[C:22]1[O:33][C:31](=[O:32])[C:25]2([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[N:24]=1

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 432420401-[(2-Benzothienylcarbonyl)amino]cyclohexanecarboxylic acid

Product 1

HCID 576728542-(2-Benzothienyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-oneYield 76.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.1 g (21 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 5 g (16 mmol) of 1-[(2-benzothienylcarbonyl)amino]cyclohexanecarboxylic acid in 50 ml of methylene chloride. After the mixture was stirred at room temperature for 4 hours, the reaction solution was concentrated under reduced pressure, ethyl acetate was added thereto, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to obtain 3.5 g (75%) of the title compound.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe mixture was successively washed with water
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6f1c0194e95d40498ea9ad47d746bc68
Source dataset
uspto-grants-2013_07
Patent number
US08481725B2

Reaction notes

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