Tetrahydrofuran → HCID 18315367, compound

HRID 275855Notes

Reaction equation

HRID 275855 reaction equation
O1CCCC1.CN(OC)[C:8](=[O:17])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH2:16].[C:20]([NH:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43](Br)[CH:42]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([Li])CCC>C(OC(=O)C)C.O.CCCCCC>[NH2:16][C:10]1[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=1[C:8]([C:45]1[CH:44]=[CH:43][CH:42]=[C:41]([CH2:40][NH:39][C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:46]=1)=[O:17]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 18315343HCID 18315343, compoundHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 18315367HCID 18315367, compoundYield 43.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran (30 ml) solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (3.22 g) and N-trityl-3-bromobenzylamine (4.28 g) was cooled to −78° C. To the solution was gradually added dropwise a hexane solution of n-butyl lithium (1.6 mol/L) (31 ml). To the mixture were then added water (70 ml) and acetic acid ethyl ester (100 ml). The organic layer was washed with water and dried over anhydrous MgSO4. The solvent was distilled off, and the residual yellow oily compound was purified by a silica gel column chromatography to give 2-amino-3′-tritylaminomethyl-5-chlorobenzophenone (2.2 g) as a yellow oily product.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. distillationThe solvent was distilled off
  4. customthe residual yellow oily compound was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-0f2613b09fa140c6934b2bb619e6b8f1
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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