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

HRID 567060
Notes
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Reaction equation

HRID 567060 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2604931-bromo-3-ethoxypropaneHCID 17786837N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethyl-methanesulfonamide

Product 1

HCID 9886441N-[6-(3-Ethoxypropoxy)-2,2-dimethylchroman-4-yl]-N-ethyl-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

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

  1. concentrationconcentrated in vac
  2. temperatureafter cooling
  3. additionthe residue was treated with water and aqueous hydrochloric acid
  4. extractionthe mixture was extracted with EA
  5. customthe organic phase was dried
  6. concentrationconcentrated
  7. customthe oily residue was chromatographed on silica gel
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes