2-Methyl-5-Nitroaniline → HCID 58550503, compound

HRID 1890996Notes

Reaction equation

HRID 1890996 reaction equation
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2][CH3:3].[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH2:18].C(N(CC)CC)C>C(#N)C.O>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH:18][S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5]

Participants

6

Reactant 3

HCID 74442-Methyl-5-NitroanilineHCID 8471TriethylamineHCID 662791-Propanesulfonyl chloride

Product 1

HCID 58550503HCID 58550503, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Propane-1-sulfonyl chloride (5.63 mL, 50 mmol) was added to a solution of 2-methyl-5-nitro-phenylamine (7.61 g, 50 mmol) and triethylamine (7 mL) in acetonitrile (100 mL). The resulting solution was vigorously stirred for 3 h at room temperature and diluted with cold water (500 mL), which lead to the formation of a precipitate. The precipitate was filtered out, washed with 1N HCl (100 mL), water (2×200 mL) and dried to give 10.2 g (79%) of propane-1-sulfonic acid (2-methyl-5-nitro-phenyl)-amide as colorless solid.

Workup

  1. filtrationThe precipitate was filtered out
  2. washwashed with 1N HCl (100 mL), water (2×200 mL)
  3. customdried

Sources & evidence

ORD record
ord-f09b1cf23cb94449ae95b831c3541ee2
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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