Triethylamine → HCID 11185309, compound

HRID 456585Notes

Reaction equation

HRID 456585 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[S:12][CH2:11][C:10](=[O:13])[NH:9][C:8]=2[CH:14]=1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[O:13]=[C:10]1[NH:9][C:8]2[CH:14]=[C:4]([CH2:3][CH2:2][O:1][S:23]([CH3:22])(=[O:25])=[O:24])[CH:5]=[CH:6][C:7]=2[S:12][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11481213HCID 11481213, compound

Product 1

HCID 11185309HCID 11185309, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (h) (0.34 g, 1.7 mmol) and triethylamine (0.25 ml, 0.19 g, 1.8 mmol) in dichloromethane (5 ml) was cooled to −15° C. and treated dropwise with methanesulfonyl chloride (0.14 ml, 1.75 mmol). The ice bath was removed and the mixture stirred 15 hours at room temperature. The organic phase was separated, washed with water, dried over magnesium sulfate and evaporated. The crude product was chromatographed on silica gel eluting with ethyl acetate/heptane (2/1) to give a white solid (0.36 g, 75%).

Workup

  1. customThe ice bath was removed
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe crude product was chromatographed on silica gel eluting with ethyl acetate/heptane (2/1)

Sources & evidence

ORD record
ord-8ddc449f8c844f4cbccbc14808d79993
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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