Triethylamine → HCID 20042519, compound

HRID 1762199Notes

Reaction equation

HRID 1762199 reaction equation
CS([Cl:5])(=O)=O.[CH3:6][O:7][C:8]([N:10]([C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:13]=1[CH2:14]O)[CH3:11])=[O:9].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:6][O:7][C:8]([N:10]([C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:13]=1[CH2:14][Cl:5])[CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 53751644HCID 53751644, compound

Product 1

HCID 20042519HCID 20042519, compoundYield 123.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride 1.7 g) in methylene chloride (3 ml) was added dropwise to a solution of 2-(N-methoxycarbonyl-N-methylamino)-6-methylbenzyl alcohol (1.04 g) and triethylamine (2.5 g) in methylene chloride (15 ml) at room temperature and the mixture was refluxed for 3 hours and the cooled. To the mixture was added an aqueous solution of sodium bicarbonate and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo to give 2-(N-methoxycarbonyl-N-methylamino)-6-methylbenzyl chloride (1.4 g).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ea86820adf81463b90dbb0ebdbd6b7e9
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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