Potassium Carbonate → N-[6-(3-Ethoxypropoxy)-2,2-dimethylchroman-4-yl]-N-ethyl-methanesulfonamide

HRID 567060Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[CH2:11][CH:10]([N:12]([CH2:17][CH3:18])[S:13]([CH3:16])(=[O:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:19])[CH:8]=2)[O:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:27]([O:29][CH2:30][CH2:31][CH2:32]Br)[CH3:28]>CC(N(C)C)=O>[CH2:27]([O:29][CH2:30][CH2:31][CH2:32][O:19][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]([CH3:1])([CH3:20])[CH2:11][CH:10]2[N:12]([CH2:17][CH3:18])[S:13]([CH3:16])(=[O:15])=[O:14])[CH3:28]

Participants

Conditions

Temperature: 110 °C

Procedure

1.5 g (5 mmol) of N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethyl-methanesulfonamide were heated to 80° C. for 30 min with 1.38 g (10 mmol) of powdered potassium carbonate in 60 ml of DMA. 4 ml of 3-ethoxy-1-bromopropane were then added dropwise at 50-60° C., the mixture was heated to 110° C. for 2 h and concentrated in vac. after cooling, the residue was treated with water and aqueous hydrochloric acid, the mixture was extracted with EA, the organic phase was dried and concentrated, and the oily residue was chromatographed on silica gel using n-heptane/EA (2:1). 0.9 g of N-[6-(3-ethoxypropoxy)-2,2-dimethylchroman-4-yl]-N-ethyl-methanesulfonamide was crystallized from appropriate fractions using petroleum ether, m.p. 72-74° C.

Workup

concentrationconcentrated in vac
temperatureafter cooling
additionthe residue was treated with water and aqueous hydrochloric acid
extractionthe mixture was extracted with EA
customthe organic phase was dried
concentrationconcentrated
customthe oily residue was chromatographed on silica gel
custom0.9 g of N-[6-(3-ethoxypropoxy)-2,2-dimethylchroman-4-yl]-N-ethyl-methanesulfonamide was crystallized from appropriate fractions

Sources & evidence

ORD record: ord-03afe92e828542c797867983fd3439bf
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06177449B1

Reaction notes

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