Benzylaniline → HCID 19024459, compound

HRID 1033803Notes

Reaction equation

HRID 1033803 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:23](Cl)=[O:24])=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:31]1([NH:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1>[CH2:38]([N:37]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:23]([N:22]([CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:6](=[O:8])(=[O:7])[NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:16][CH:17]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:24])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 66028BenzylanilineHCID 81531DiisopropylethylamineHCID 19024475HCID 19024475, compound

Product 1

HCID 19024459HCID 19024459, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 75 mg (0.166 mmole) of N-[[2'-(N-t-butylsulfamoyl)biphenyl-4-yl]methyl]-N-pentylcarbamoyl chloride (from Step B), 46 mg (0.25 mmole) of N-phenylbenzylamine, 58 μL (43 mg, 0.33 mmole) of N,N-diisopropylethylamine, and 1 mL of dry toluene was stirred under N2 at 110° C. for 48 hours. The cooled reaction mixture was concentrated by rotary evaporation. Flash chromatography of the residual oil on silica gel (elution with 4:1 and then 3:1 hexane-EtOAc) gave 91 mg (92%) of the title compound as a tacky foam, homogeneous by TLC in 3:1 hexane-EtOAc; FAB-MS m/e 599 (M+1)+.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated by rotary evaporation
  3. washFlash chromatography of the residual oil on silica gel (elution with 4:1

Sources & evidence

ORD record
ord-37d5264a32a64cbeb0e1ed75b9757acf
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

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