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Tetrahydrofuran → 2-Amino-3'-tert-butoxycarbonylamino-5-chlorobenzophenone

HRID 275846
Notes
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Reaction equation

HRID 275846 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]([O:24][C:25]([NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30](Br)[CH:29]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21].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:32]1[CH:31]=[CH:30][CH:29]=[C:28]([NH:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])[CH:33]=1)=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 2757254N-(tert-Butoxycarbonyl)-3-bromoanilineHCID 222266052-amino-5-chloro-N-methoxy-N-methylbenzamideHCID 178418339Butyllithium

Product 1

HCID 183153632-Amino-3'-tert-butoxycarbonylamino-5-chlorobenzophenoneYield 14.5%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8058HexaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran (30 ml) solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (4.3 g) and N-tert-butoxycarbonyl-3-bromoaniline (3.79 g) was cooled to −78° C. To the solution was gradually added dropwise a hexane solution of n-butyl lithium (1.6 mol/L) (42 ml). To the mixture were added water (100 ml) and acetic acid ethyl ester (300 ml). The organic layer was washed with water and dried over anhydrous MgSO4. The _solvent was then distilled off, and the residue was purified by means of a silica gel column chromatography to give 2-amino-3′-tert-butoxycarbonylamino-5-chlorobenzophenone (0.7 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 then distilled off
  4. customthe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-31e7144020c14cf69fe2bf4699aa52f4
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06352982B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes