Water → N-(2,2-dimethoxyethyl)-6-chloro-2-naphthalenesulfonamide

HRID 2086224Notes

Reaction equation

HRID 2086224 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].C(N(CC)CC)C.[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([S:26](Cl)(=[O:28])=[O:27])[CH:20]=[CH:19]2.O>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:5][S:26]([C:21]1[CH:20]=[CH:19][C:18]2[C:23](=[CH:24][CH:25]=[C:16]([Cl:15])[CH:17]=2)[CH:22]=1)(=[O:27])=[O:28]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 106351296-Chloronaphthalene-2-sulfonyl chloride

Product 1

HCID 22727126N-(2,2-dimethoxyethyl)-6-chloro-2-naphthalenesulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,2-dimethoxyethylamine (3 g) and triethylamine (4.318 g) in tetrahydrofuran (120 ml) was treated portionwise at 0° C. with 6-chloronaphthalene-2-sulfonyl chloride (7.45 g) and stirred at 0° C. for 30 minutes. The reaction mixture was combined with water and ethyl acetate to separate the organic phase, which was washed with an aqueous solution of citric acid and brine, dried and concentrated to obtain N-(2,2-dimethoxyethyl)-6-chloro-2-naphthalenesulfonamide as a colorless oil.

Workup

  1. customto separate the organic phase, which
  2. washwas washed with an aqueous solution of citric acid and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5d9884b28cb743bea128fd4c63a88c05
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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