Aniline → HCID 69586673, compound

HRID 2216222Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][O:9][C:10]([C:12]1[S:13][C:14]([S:31][CH3:32])=[C:15]([S:17]([C:20]2[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[C:23](Cl)=[C:22]([Br:30])[CH:21]=2)(=[O:19])=[O:18])[CH:16]=1)=[O:11].C([O-])(=O)C.[Na+]>O1CCOCC1>[CH3:8][O:9][C:10]([C:12]1[S:13][C:14]([S:31][CH3:32])=[C:15]([S:17]([C:20]2[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[C:23]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:22]([Br:30])[CH:21]=2)(=[O:19])=[O:18])[CH:16]=1)=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of aniline (112 mg, 1.35 mmol), 4-(3-bromo-4-chloro-5-nitro-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester ((Example 318: step c) 53 mg, 0.11 mmol), and sodium acetate (16.5 mg, 0.2 mmol) in dioxane (3 mL) was heated at 80° C. for 24 h. The mixture was partitioned between EtOAc (50 mL) and 0.5 N HCl (10 mL) and the organic layer was further extracted with 0.5 N HCl (2×10 mL), NaHCO3 (10 mL), and brine (20 mL). Drying of the solution over sodium sulfate followed by concentration yielded the product (58 mg) which was used without further purification. 1H-NMR (CDCl3): δ 8.04 (s, 1H), 7.64 (d, 1H, J=2.1 Hz), 7.32 (d, 1H, J=1.9 Hz), 7.25 (m, 2H), 6.95 (m, 1H), 6.69 (m, 2H), 5.70) (s, 1H), 3.90 (s, 3H), 2.66 (s, 3H).

Workup

customThe mixture was partitioned between EtOAc (50 mL) and 0.5 N HCl (10 mL)
extractionthe organic layer was further extracted with 0.5 N HCl (2×10 mL), NaHCO3 (10 mL), and brine (20 mL)
dry with materialDrying of the solution over sodium sulfate
concentrationfollowed by concentration

Sources & evidence

ORD record: ord-a40bf7129d70401da6a320e2ab700631
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109354B2

Reaction notes

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