2,4-Dichlorobenzylamine → HCID 25096465, compound

HRID 2081061Notes

Reaction equation

HRID 2081061 reaction equation
[CH3:1][N:2]1[CH:6]([C:7]([OH:9])=O)[CH2:5][N:4]([CH:10]([CH3:12])[CH3:11])[C:3]1=[O:13].C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[CH2:53][NH2:54]>ClCCl>[Cl:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[CH2:53][NH:54][C:7]([CH:6]1[CH2:5][N:4]([CH:10]([CH3:12])[CH3:11])[C:3](=[O:13])[N:2]1[CH3:1])=[O:9]

Participants

7

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67103622HCID 67103622, compound

Product 1

HCID 25096465HCID 25096465, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 3-methyl-1-(1-methylethyl)-2-oxo-4-imidazolidinecarboxylic acid (100 mg, 0.537 mmol), N-ethylmorpholine (0.274 ml, 2.148 mmol), 1-hydroxybenzotriazole hydrate (99 mg, 0.644 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (124 mg, 0.644 mmol) in dichloromethane (9 ml) was stirred at room temperature for 10 minutes. A solution of [1-(2,4-dichlorophenyl)methyl]amine (95 mg, 0.537 mmol) in dichloromethane (1 ml) was added and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane (10 ml) and the mixture was washed with saturated sodium hydrogen carbonate solution (10 ml) and brine (10 ml), dried and evaporated. The residue was purified by mass-directed automated HPLC. The residue was triturated with ether and the resulting solid was collected and dried to give N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-(1-methylethyl)-2-oxo-4-imidazolidinecarboxamide (124 mg, 67%). LCMS [M+H]+=344, retention time=2.32 minutes.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. washthe mixture was washed with saturated sodium hydrogen carbonate solution (10 ml) and brine (10 ml)
  3. customdried
  4. customevaporated
  5. customThe residue was purified
  6. customThe residue was triturated with ether
  7. customthe resulting solid was collected
  8. customdried

Sources & evidence

ORD record
ord-86b7266e7f684a7bafe19c38c3bc4f2d
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

Loading…