3,4-Dichloroaniline → Tert-butyl 2-(4-(4-((3,4-dichlorophenyl)carbamoyl)phenoxy)-3-(methylsulfonamidomethyl)phenyl)acetate

HRID 453494Notes

Reaction equation

HRID 453494 reaction equation
[C:1]([O:5][C:6](=[O:30])[CH2:7][C:8]1[CH:23]=[CH:22][C:11]([O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)=[C:10]([CH2:24][NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[Cl:37][C:38]1[CH:39]=[C:40]([NH2:45])[CH:41]=[CH:42][C:43]=1[Cl:44]>C(Cl)Cl.CN(C=O)C>[Cl:37][C:38]1[CH:39]=[C:40]([NH:45][C:17]([C:16]2[CH:15]=[CH:14][C:13]([O:12][C:11]3[CH:22]=[CH:23][C:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:30])=[CH:9][C:10]=3[CH2:24][NH:25][S:26]([CH3:29])(=[O:27])=[O:28])=[CH:21][CH:20]=2)=[O:19])[CH:41]=[CH:42][C:43]=1[Cl:44]

Participants

6

Reactant 3

HCID 72573,4-DichloroanilineHCID 65578Oxalyl chlorideHCID 684645984-(4-(2-Tert-butoxy-2-oxoethyl)-2-(methylsulfonamido-methyl)phenoxy)benzoic acid

Product 1

HCID 68463349Tert-butyl 2-(4-(4-((3,4-dichlorophenyl)carbamoyl)phenoxy)-3-(methylsulfonamidomethyl)phenyl)acetateYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The product of step D (62 mg, 0.14 mmol) was diluted with methylene chloride (1 mL) followed by the addition of oxalyl dichloride (0.093 mL, 0.19 mmol) and 1 drop of DMF. The reaction was stirred for 30 minutes followed by the addition of 3,4-dichlorobenzenamine (46 mg, 0.28 mmol). The reaction was allowed to stir for 1 hour. The reaction mixture was loaded directly onto a 12i sim and purified on the horizon eluting with methylene chloride:MeOH (99.5-0.5 to 95:5) to yield 30 mg of tert-butyl 2-(4-(4-((3,4-dichlorophenyl)carbamoyl)phenoxy)-3-(methylsulfonamidomethyl)phenyl)acetate as a clear oil.

Workup

  1. stirringto stir for 1 hour
  2. custompurified on the horizon
  3. washeluting with methylene chloride

Sources & evidence

ORD record
ord-456aba8a9a4241229b3272815b757f0e
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

Loading…