Triethylamine → 4,8-Dichloro-5-methyl-6-ethoxycarbonylthiochroman

HRID 1275461Notes

Reaction equation

HRID 1275461 reaction equation
O[CH:2]1[C:11]2[C:6](=[C:7]([Cl:18])[CH:8]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]=2[CH3:12])[S:5][CH2:4][CH2:3]1.C(N(CC)CC)C.CS([Cl:30])(=O)=O>C(Cl)Cl>[Cl:30][CH:2]1[C:11]2[C:6](=[C:7]([Cl:18])[CH:8]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]=2[CH3:12])[S:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 234506678-Chloro-6-ethoxycarbonyl-5-methylthiochroman-4-ol

Product 1

HCID 221183894,8-Dichloro-5-methyl-6-ethoxycarbonylthiochromanYield 116.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 Gram (3.5 mmol) of 4-hydroxy-5-methyl-6-ethoxycarbonyl-8-chlorothiochroman was dissolved in 5 ml of methylene chloride, and 0.72 ml (5.2 mmol) of triethylamine and 0.4 ml (5.2 mmol) of methanesulfonyl chloride were added with an ice bath cooling. The mixture was stirred at room temperature for 1 hour. After the completion of the reaction, an organic layer was washed with 2N hydrochloric acid and with a saturated sodium hydrogencarbonate aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off to give 1.24 g (yield 100%) of 4,8-dichloro-5-methyl-6-ethoxycarbonylthiochroman.

Workup

  1. temperaturecooling
  2. customAfter the completion of the reaction
  3. washan organic layer was washed with 2N hydrochloric acid and with a saturated sodium hydrogencarbonate aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-f78baf194a5f43f8a5b957b850dcd66e
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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