Iodine → HCID 66905441, compound

HRID 1690582Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[O-]S([O-])(=O)=O.[Na+].[Na+].[F:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[C:19]([N+:25]([O-])=O)[CH:18]=1.[In].II>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:21]2[N:5]([C:4]3[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=3)[N:25]=[C:19]3[C:20]=2[CH:23]=[CH:24][C:17]([F:16])=[CH:18]3)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

3-Chloroaniline (12.4 ml, 118 mmol; [108-42-9]) and Na2SO4 (3.36 g, 24 mmol) were added to a solution of 4-fluoro-2-nitro-benzaldehyde (1 g, 6 mmol; [2923-96-8]) in THF (12 ml) under an argon atmosphere. The suspension was stirred at 50° C. for 16 h. Na2SO4 was removed, indium (2.04 g, 18 mmol) and iodine (1.2 g, 5 mmol) were added and the reaction mixture was stirred at 50° C. for 24 h. The mixture was filtered over celite and the filtrate was poured onto 1 M aqueous HCl solution/iPrOAc 1/1. The aqueous layer was extracted one more time with iPrOAc and the combined extracts were washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by crystallization (CH2Cl2) to give the title compound (672 mg, 1.8 mmol; 31%) as white powder. MS: m/e=372.0 [M+H+].

Workup

customNa2SO4 was removed
stirringthe reaction mixture was stirred at 50° C. for 24 h
filtrationThe mixture was filtered over celite
additionthe filtrate was poured onto 1 M aqueous HCl solution/iPrOAc 1/1
extractionThe aqueous layer was extracted one more time with iPrOAc
washthe combined extracts were washed with brine
dry with materialdried over Na2SO4
customThe solvent was removed under reduced pressure
customthe residue was purified by crystallization (CH2Cl2)

Sources & evidence

ORD record: ord-308978fe471544c5b7ecc0307822cb19
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153663B2

Reaction notes

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