Ethanol → tert-butyl N-[4-[3-(4-amino-2-chloro-6-methylphenyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 2216051Notes

Reaction equation

[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]([C:10]1[S:11][C:12]([S:35][CH3:36])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([N+:31]([O-])=O)=[CH:26][C:25]=3[Cl:34])[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].CCO.[Cl-].[NH4+]>[Fe].O>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]([C:10]1[S:11][C:12]([S:35][CH3:36])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([NH2:31])=[CH:26][C:25]=3[Cl:34])[CH:21]=[CH:22][CH:23]=2)(=[O:16])=[O:17])[CH:14]=1)=[NH:9])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

{[4-(2′-Chloro-6′-methyl-4′-nitro-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (20 mg, 0.034 mmol, Example 134: step a) was dissolved into EtOH (2 mL). To this was added ammonium chloride (18 mg, 0.34 mmol) dissolved into water (4 mL). The reaction was heated to 50° C. and iron (9.6 mg, 0.34 mmol) was added. The reaction was then heated to 80° C. for 12 hours followed by filtration through celite with methanol and EtOAc. The solvents were removed in vacuo resulting in desired product that was used with out further purification or characterization.

Workup

temperatureThe reaction was then heated to 80° C. for 12 hours
filtrationfollowed by filtration through celite with methanol and EtOAc
customThe solvents were removed in vacuo

Sources & evidence

ORD record: ord-32373234a94a425da1881aec14a9b900
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109354B2

Reaction notes

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