Triethylamine → HCID 21714287, compound

HRID 355695Notes

Reaction equation

HRID 355695 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:19])=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10]2.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:27][S:28]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:19])=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10]2)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21714272HCID 21714272, compound

Product 1

HCID 21714287HCID 21714287, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

A mixture of ethyl 7-(2-hydroxyethoxy)-4-methyl-1H-indole-2-carboxylate (1.10 g, 4.18 mmol), triethylamine (0.93 g, 9.19 mmol) and dichloromethane (30 ml) was cooled to -10° C., after which methanesulfonyl chloride (0.57 g, 5.01 mmol) was added dropwise with stirring at -10° C. After completion of the dropwise addition, the resulting mixture was stirred at -10° C. for another 2 hours and the reaction mixture was poured into ice water, followed by extraction with chloroform (three times). The extract solution was washed successively with a saturated aqueous ammonium chloride solution, a saturated aqueous sodium hydrogen-carbonate solution and a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain ethyl 7-(2-methanesulfonyloxyethoxy)-4-methyl-1H-indole-2-carboxylate. This compound was used in the subsequent reaction without further purification.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringthe resulting mixture was stirred at -10° C. for another 2 hours
  3. extractionfollowed by extraction with chloroform (three times)
  4. washThe extract solution was washed successively with a saturated aqueous ammonium chloride solution
  5. dry with materiala saturated aqueous sodium hydrogen-carbonate solution and a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-30aff35a57cd467b8188151d24275fff
Source dataset
uspto-grants-1998_11
Patent number
US05834454

Reaction notes

Loading…