Phenethylamine → HCID 68579559, compound

HRID 643995Notes

Reaction equation

HRID 643995 reaction equation
CCN=C=NCCCN(C)C.[C:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]2[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=2[C:27]([O:29][CH3:30])=[O:28])(=[O:23])=[O:22])=[CH:17][CH:16]=1)(O)=[O:13].ON1C2N=CC=CC=2N=N1.[CH2:45]([NH2:53])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.O>[CH3:30][O:29][C:27](=[O:28])[C:26]1[CH:31]=[CH:32][CH:33]=[CH:34][C:25]=1[NH:24][S:21]([C:18]1[CH:19]=[CH:20][C:15]([C:12](=[O:13])[NH:53][CH2:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:16][CH:17]=1)(=[O:22])=[O:23]

Participants

8

Reactant 5

HCID 1001PhenethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 17564401HCID 17564401, compound

Product 1

HCID 68579559HCID 68579559, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDCI (84.4 mg, 0.44 mmol) is added to a solution of the title A compound, followed by methyl 2-(4-carboxy-benzene-sulfonylamino)-benzoate (134.1 mg, 0.40 mmol) and 1-hydroxy-7-azabenzotriazole (HOAt, 59.9 mg, 0.44 mmol) in 1 mL of DMF at RT. The reaction is stirred 1 h after which phenethylamine (50.2 μL, 0.40 mmol) is added. The resulting solution is stirred overnight at RT, followed by addition of 5% aqueous sodium bicarbonate (1 mL) and water (8 mL). A white precipitate is collected by filtration, washed with water, and dried under vacuum to give 2-(4-phenethylcarbamoylbenzenesulfonyl-amino)-benzoic acid methyl ester m.p. 167-168° C.

Workup

  1. additionis added
  2. filtrationA white precipitate is collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-69e4b93163294066ae3292139727ff24
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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