Triethylamine → 6-Butoxy-4-(methylsulfonyl)amino-2,2-dimethylchroman

HRID 618824Notes

Reaction equation

HRID 618824 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:10]=2)[O:5][C:4]([CH3:18])([CH3:17])[CH2:3]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C1COCC1>[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[O:5][C:4]([CH3:17])([CH3:18])[CH2:3][CH:2]2[NH:1][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 218486564-Amino-6-butoxy-2,2-dimethylchroman

Product 1

HCID 218486886-Butoxy-4-(methylsulfonyl)amino-2,2-dimethylchromanYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A reaction mixture of 3.0 g (12 mmol) of 4-amino-6-butoxy-2,2-dimethylchroman, 4.9 g (48 mmol) of triethylamine and 1.65 g (14.4 mmol) of methanesulfonyl chloride in 25 ml of THF was stirred at RT for 3 h. After concentrating, the residue was taken up in water and extracted with EA. After drying and concentrating, the product was crystallized using PE and 2.25 g of 6-butoxy-4-(methylsulfonyl)amino-2,2-dimethylchroman were obtained; m.p. 123-127° C.

Workup

  1. concentrationAfter concentrating
  2. extractionextracted with EA
  3. customAfter drying
  4. concentrationconcentrating
  5. customthe product was crystallized

Sources & evidence

ORD record
ord-fa3094ca7314413dbc518e7986b9fd82
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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