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

HRID 1968852Notes

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-aminobenzenethiol (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.

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-0ed90adb6fad477696595a4ce9366913
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426429B2

Reaction notes

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