2,4-Dichlorobenzylamine → 1-[3-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-3-(2,4-dichloro-benzyl)-urea

HRID 898569Notes

Reaction equation

HRID 898569 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH2:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14].C(N(CC)CC)C.[Cl:25][C:26]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:27]=1[CH2:28][NH2:29].CN([CH:38]=[O:39])C>C1COCC1>[Cl:2][C:3]1[CH:4]=[C:5]([NH:17][C:38]([NH:29][CH2:28][C:27]2[CH:30]=[CH:31][C:32]([Cl:34])=[CH:33][C:26]=2[Cl:25])=[O:39])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 14852,4-DichlorobenzylamineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 688758613-Chloro-4-[2-(diethylamino)ethoxy]aniline hydrochloride

Product 1

HCID 596916661-[3-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-3-(2,4-dichloro-benzyl)-urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

203 mg (1.236 mmol) of CDT in 4 mL DMF was added to a solution of 345 mg (1.236 mmol) of 3-chloro-4-(2-diethylamino-ethoxy)-phenylamine-hydrochloride (intermediate product Z1b) and 0.56 mL (4.000 mmol) of triethylamine in 40 mL THF and the mixture was stirred for 2 hours at RT. 176 mg (1.236 mmol) of 2,4-dichloro-benzylamine was added, the reaction mixture was refluxed for 4 hours and then evaporated down i. vac. The residue was purified by column chromatography (silica gel, dichloromethane/MeOH/conc. aqueous ammonia 80:20:1) and the product was triturated with diisopropylether.

Workup

  1. temperaturethe reaction mixture was refluxed for 4 hours
  2. customevaporated down i
  3. customThe residue was purified by column chromatography (silica gel, dichloromethane/MeOH/conc. aqueous ammonia 80:20:1)
  4. customthe product was triturated with diisopropylether

Sources & evidence

ORD record
ord-d838cfb00d424732bcd922dda114263b
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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