Triethylamine → HCID 15037082, compound

HRID 1534341Notes

Reaction equation

HRID 1534341 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH:7]([C:20]1[CH:24]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:22][CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([NH:6][CH:7]([C:20]1[CH:24]=[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:22][CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 150370773-(1-Aminotridecyl)-5-trimethylsilylfuran

Product 1

HCID 15037082HCID 15037082, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (37 μl, 0.48 mmol) was added to a solution of 3-(1-aminotridecyl)-5-trimethylsilylfuran (134.6 mg, 0.4 mmol) and triethylamine (67 μl, 0.48 mmol) in dichloromethane (2 ml) at 0°. Stirring continued overnight (14 hours) while the cooling both attained room temperature. The reaction mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave an oil, which was purified by flash chromatography on silica using 10% ethyl ether/hexane. Fractions with Rf of about 0.07 on evaporation gave the title sulfonamide as a pale yellow oil.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionExtraction (ethyl ether) and evaporation of the
  3. dry with materialdried (magnesium sulfate)
  4. customextracts gave an oil, which
  5. customwas purified by flash chromatography on silica using 10% ethyl ether/hexane
  6. customFractions with Rf of about 0.07 on evaporation

Sources & evidence

ORD record
ord-7481f22f8a1b49d5ab74b1515c6c9c2d
Source dataset
uspto-grants-1992_02
Patent number
US05089485

Reaction notes

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