Benzenesulfonyl chloride → HCID 58625075, compound

HRID 390266Notes

Reaction equation

HRID 390266 reaction equation
[CH3:1][O:2][CH:3]([O:21][CH3:22])[C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[O:7][C:8]1[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=1.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH3:22][O:21][CH:3]([O:2][CH3:1])[C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[O:7][C:8]1[CH:9]=[C:10]([NH:14][S:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 586250523-(3-Dimethoxymethyl-4-nitro-phenoxy)phenylamine

Product 1

HCID 58625075HCID 58625075, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-(3-dimethoxymethyl-4-nitro-phenoxy)-phenylamine (0.013 mol) in THF (100 mL) and TEA (200 mL) was stirred at room temperature and a mixture of benzenesulfonyl chloride (0.013 mol) in THF (50 mL) was added dropwise, then the reaction mixture was stirred overnight at room temperature and again overnight at 60° C. The solvent was evaporated and the residue was stirred in H2O. After extraction with CH2Cl2, the organic layer was separated, dried, filtered off and the solvent was evaporated. The residue was purified by Biotage column chromatography (eluent: CH2Cl2 100%). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. additionwas added dropwise
  2. stirringthe reaction mixture was stirred overnight at room temperature and again overnight at 60° C
  3. customThe solvent was evaporated
  4. stirringthe residue was stirred in H2O
  5. extractionAfter extraction with CH2Cl2
  6. customthe organic layer was separated
  7. customdried
  8. filtrationfiltered off
  9. customthe solvent was evaporated
  10. customThe residue was purified by Biotage column chromatography (eluent: CH2Cl2 100%)
  11. customThe purest product fractions were collected
  12. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5d1ca30f4db8464d82d089902145a35c
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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