Triethylamine → HCID 58981681, compound

HRID 1816363Notes

Reaction equation

HRID 1816363 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([C:14]#[C:15][CH2:16][CH2:17][OH:18])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([C:14]#[C:15][CH2:16][CH2:17][O:18][S:27]([CH3:26])(=[O:29])=[O:28])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22493473HCID 22493473, compound

Product 1

HCID 58981681HCID 58981681, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 500-mL 1-necked round-bottom flask was equipped with a magnetic stirring bar and rubber septum with a nitrogen inlet. The vessel was charged with the product of Example 6 (13.6 g), dichloromethane (100 mL) and triethylamine (8.43 mL). The reaction mixture was cooled to 0° C. in an ice bath, and a solution of methanesulfonyl chloride (6.93 g) in dichloromethane (10 mL) was added in drops over 30 min. The cooling was removed and the reaction mixture was allowed to warm up to room temperature. After 1 h when TLC indicated complete conversion, 50 mL ice water was added, and the reaction mixture was transferred to a 500-mL separatory funnel. The organic extract was separated and washed with aqueous NaHCO3, brine, and dried over MgSO4. After filtration, the solvents were evaporated under reduced pressure (rotary evaporator, 30° C.) to obtain the title compound as pale yellow gum (17.5 g).

Workup

  1. customA 500-mL 1-necked round-bottom flask was equipped with a magnetic stirring bar
  2. customThe cooling was removed
  3. temperatureto warm up to room temperature
  4. additionconversion, 50 mL ice water was added
  5. customthe reaction mixture was transferred to a 500-mL separatory funnel
  6. extractionThe organic extract
  7. customwas separated
  8. washwashed with aqueous NaHCO3, brine
  9. dry with materialdried over MgSO4
  10. filtrationAfter filtration
  11. customthe solvents were evaporated under reduced pressure (rotary evaporator, 30° C.)

Sources & evidence

ORD record
ord-3e4716d1824f43e186ed960125e2c542
Source dataset
uspto-grants-2005_04
Patent number
US06884803B2

Reaction notes

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