Tetrahydrofuran → 1-[3-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-3-(2-chloro-4-trifluoromethyl-benzyl)-urea

HRID 898615Notes

Reaction equation

HRID 898615 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[Cl:14][C:15]1[CH:16]=[C:17]([NH2:29])[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26].C1C[O:33][CH2:32]C1>>[Cl:14][C:15]1[CH:16]=[C:17]([NH:29][C:32]([NH:5][CH2:4][C:3]2[CH:6]=[CH:7][C:8]([C:10]([F:11])([F:12])[F:13])=[CH:9][C:2]=2[Cl:1])=[O:33])[CH:18]=[CH:19][C:20]=1[O:21][CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 167916763-Chloro-4-(2-diethylaminoethoxy)phenylamineHCID 22337564(2-Chloro-4-(trifluoromethyl)phenyl)methanamine

Product 1

HCID 596916021-[3-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-3-(2-chloro-4-trifluoromethyl-benzyl)-urea

Procedure

0.770 g (4.457 mmol) CDT was added at 0° C. to a solution of 0.870 g (4.151 mmol) 2-chloro-4-trifluoromethyl-benzylamine (Example 168a) in 50 mL abs. THF and the mixture was stirred for 1 h at RT. 1.080 g (4.449 mmol) 3-chloro-4-(2-diethylamino-ethoxy)-phenylamine (Z1b) was added and the mixture was refluxed for 5 h. The reaction mixture was evaporated down i. vac. and the residue was taken up in dichloromethane. The org. phase was washed with 15% aqueous potassium carbonate, dried over sodium sulphate and evaporated down i. vac.

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. customThe reaction mixture was evaporated down i
  3. washphase was washed with 15% aqueous potassium carbonate
  4. dry with materialdried over sodium sulphate
  5. customevaporated down i

Sources & evidence

ORD record
ord-1cc07c9fbd0e477a8019820c145983fa
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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