Water → HCID 86669371, compound

HRID 574101Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:15]([N+:16]([O-])=O)=[C:14]([F:19])[CH:13]=[C:12]([O:20][CH3:21])[C:11]=1[F:22].[O-]S(S([O-])=O)=O.[Na+].[Na+].O>CCO>[F:19][C:14]1[CH:13]=[C:12]([O:20][CH3:21])[C:11]([F:22])=[C:10]([NH:9][C:3]2[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=2[F:1])[C:15]=1[NH2:16]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 2-fluoro-N-(2,5-difluoro-3-methoxy-6-nitrophenyl)-4-iodobenzeneamine (12.5 g, 29.5 mmol) in EtOH (200 mL) was heated at 70° C. to form a clear transparent solution and to this hot solution was added dropwise a freshly prepared solution of Na2S2O4 in water (15 g, 86 mmol, in 30 mL). The mixture was further heated for 1 h at 90° C. Upon cooling to room temperature the mixture was concentrated to remove ethanol under reduced pressure. The residue was diluted with ethyl acetate (25 mL), washed with water and brine, The organic layer was separated, dried over MgSO4 and concentrated under reduced pressure to yield off white solid (10.2 g, 88%). The solid was used as was in the next reaction without purification.

Workup

customto form a clear transparent solution
temperatureThe mixture was further heated for 1 h at 90° C
temperatureUpon cooling to room temperature the mixture
concentrationwas concentrated
customto remove ethanol under reduced pressure
additionThe residue was diluted with ethyl acetate (25 mL)
washwashed with water and brine
customThe organic layer was separated
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-46583b35d81e4f3ab73c87dc23c2f719
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034861B2

Reaction notes

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