Triethylamine → HCID 89560543, compound

HRID 590401Notes

Reaction equation

HRID 590401 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH:14]=[O:15])=[CH:13][C:8]=2[S:7][C:6]1=[O:16].CCN(CC)CC.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:24][S:25]([O:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH:14]=[O:15])=[CH:13][C:8]=2[S:7][C:6]1=[O:16])(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 89560616HCID 89560616, compound2×

Product 1

HCID 89560543HCID 89560543, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(3-hydroxypropyl)-2-oxo-2,3-dihydro-1,3-benzothiazole-6-carbaldehyde (Intermediate 71, 158 mg, 0.67 mmol) in CH2Cl2 (5 mL) was added Et3N (0.11 mL, 0.80 mmol) and the mixture was cooled to 0° C. To this solution, methanesulfonyl chloride was added dropwise (57 μL, 0.74 mmol) and the mixture was maintained at 0° C. for 90 min. CH2Cl2 and 4% aqueous sodium bicarbonate solution (10 mL) were added to the reaction mixture and stirred for 10 min. The two layers were separated and the organic phase was washed with water and brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give the title compound as a colourless oil (243 mg, 99% yield) which was used without further purification.

Workup

  1. temperaturethe mixture was maintained at 0° C. for 90 min
  2. customThe two layers were separated
  3. washthe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d96b328fddf44cf1b466cef56bd14134
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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