4-Nitrobenzenesulfonyl chloride → HCID 22390615, compound

HRID 1071941Notes

Reaction equation

HRID 1071941 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][CH2:10][CH2:11][NH:12][CH3:13].[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15]>C(Cl)Cl>[CH3:8][O:9][CH2:10][CH2:11][N:12]([CH3:13])[S:23]([C:20]1[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:22][CH:21]=1)(=[O:24])=[O:25]

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 300977(2-Methoxyethyl)(methyl)amine

Product 1

HCID 22390615HCID 22390615, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of triethylamine (2.4 ml, 17.23 mmol) and N-(2-methoxyethyl)methylamine (1.5 g, 16.85 mmol) in DCM (20 ml) was cooled in an ice/water bath. A solution of 4-nitrobenzenesulphonyl chloride (3.2 g, 14.45 mmol) in DCM (20 ml) was added dropwise. The reaction was stirred for one hour the cooling bath was removed and the mixture stirred for further 3 hours. The reaction mixture was washed with 1M hydrochloric acid (40 ml), water (30 ml) and then brine. The volatiles were evaporated to give the title compound (3.8 g). M/z: 245.

Workup

  1. customwas removed
  2. stirringthe mixture stirred for further 3 hours
  3. washThe reaction mixture was washed with 1M hydrochloric acid (40 ml), water (30 ml)
  4. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-fb049011889b4b6cbe8d451067c91be7
Source dataset
uspto-grants-2005_06
Patent number
US06908920B2

Reaction notes

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