Water → 3-(3-Dimethoxymethyl-4-nitro-phenylsulfanyl)-phenylamine

HRID 390224Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[NH2:7][C:8]1[CH:9]=[C:10]([SH:14])[CH:11]=[CH:12][CH:13]=1.Cl[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH:25]([O:28][CH3:29])[O:26][CH3:27])[CH:17]=1.O>CC(N(C)C)=O>[CH3:29][O:28][CH:25]([O:26][CH3:27])[C:18]1[CH:17]=[C:16]([S:14][C:10]2[CH:9]=[C:8]([NH2:7])[CH:13]=[CH:12][CH:11]=2)[CH:21]=[CH:20][C:19]=1[N+:22]([O-:24])=[O:23]

Participants

Conditions

Temperature: 80 °C

Procedure

K2CO3 (0.085 mol) was added to a mixture of 3-aminothiophenol (0.075 mol) in DMA (150 mL), then 4-chloro-2-dimethoxymethyl-1-nitrobenzene (0.050 mol) was added and the reaction mixture was stirred for 2 hours at 80° C. H2O was added and the mixture was extracted with diisopropyl ether. The crude product was purified by column chromatography (eluent: 70:30 CH2Cl2:hexane up to 99:1 CH2Cl2:CH3OH). The product fractions were collected and the solvent was evaporated to yield the title compound as a residue which contained about 10% of an impurity. (The product was used in subsequent steps without further purification.)

Workup

extractionthe mixture was extracted with diisopropyl ether
customThe crude product was purified by column chromatography (eluent
customThe product fractions were collected
customthe solvent was evaporated

Sources & evidence

ORD record: ord-18e592eb6de3446d97b30229bd12fce6
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383637B2

Reaction notes

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