Triethylamine → HCID 86628048, compound

HRID 2078420Notes

Reaction equation

HRID 2078420 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 28414031HCID 28414031, compound

Product 1

HCID 86628048HCID 86628048, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

4-[(2-Hydroxyethoxy)methyl]benzonitrile (5.5 g, 30.5 mmol; see step (i) above) was dissolved in DCM (61 mL) and cooled to −10° C. Triethylamine (5 mL, 36.5 mmol) and methanesulfonyl chloride (3.84 g, 33.5 mmol) were added and the resulting mixture was stirred at below −5° C. for 1.5 h and then at RT overnight. Dichloromethane (200 mL) was added and the mixture was washed with water (2×100 mL) and then dried over Na2SO4. Evaporation of solvents gave 7.3 g (94%) of the title compound, which was used without further purification.

Workup

  1. customat RT
  2. customovernight
  3. washthe mixture was washed with water (2×100 mL)
  4. dry with materialdried over Na2SO4
  5. customEvaporation of solvents

Sources & evidence

ORD record
ord-0ba14a67b71840baaf38da53dca4e3e8
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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