Dichloromethane → HCID 67264251, compound

HRID 1041112Notes

Reaction equation

HRID 1041112 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([NH2:9])[CH:8]=1.C(N(CC)CC)C.C(Cl)Cl.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:10]([O-:12])=[O:11])=[C:7]([N:9]([S:24]([CH3:23])(=[O:26])=[O:25])[S:24]([CH3:23])(=[O:26])=[O:25])[CH:8]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 853005-Methoxy-2-nitroaniline

Product 1

HCID 67264251HCID 67264251, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 5-Methoxy-2-nitro-phenylamine (5.0 g, 0.030 mol) and Triethylamine (10.0 mL, 0.0717 mol) in Methylene chloride (100 mL, 2 mol) at 0° C. was added dropwise Methanesulfonyl chloride (5.1 mL, 0.065 mol). The mixture was stirred for 18 hours. The mixture was poured into 1N Hydrochloric Acid (200 mL). The aqueous was extracted with dichloromethane (3×100 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated. The oil was purified by silica gel chromatography using 20%→100% Ethyl Acetate:Hexane solvent gradient. N-(5-Methoxy-2-nitro-phenyl)-N-(methylsulfonyl) methanesulfonamide isolated as a yellow solid (7.75 g, 80%).

Workup

  1. extractionThe aqueous was extracted with dichloromethane (3×100 mL)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-576a86f14a14419cbbf164bae1a0aefe
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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