Bis(2-Methoxyethyl)amine → 3-[[Bis(2-methoxyethyl)amino]methyl]-2-(4-methoxyphenylmethyl)-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide

HRID 1736014Notes

Reaction equation

HRID 1736014 reaction equation
O[CH2:2][C:3]1(CO)[CH2:8][C:7]2[CH:9]=[CH:10][S:11][C:6]=2[S:5](=[O:13])(=[O:12])[N:4]1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[CH3:41][O:42][CH2:43][CH2:44][NH:45][CH2:46][CH2:47][O:48][CH3:49]>C1COCC1>[CH3:41][O:42][CH2:43][CH2:44][N:45]([CH2:2][C:3]1[N:4]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[S:5](=[O:13])(=[O:12])[C:6]2[S:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)[CH2:46][CH2:47][O:48][CH3:49]

Participants

6

Reactant 4

HCID 2383Bis(2-Methoxyethyl)amineHCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 677348383-Hydroxymethyl-2-(4-methoxyphenylmethyl)-2H-thieno[3,2-e]-1,2-thiazine-3-methanol 1,1-dioxide

Product 1

HCID 194340083-[[Bis(2-methoxyethyl)amino]methyl]-2-(4-methoxyphenylmethyl)-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step C (1.60 g, 4.75 mmol) and triethylamine (1.44 g, 14.2 mmol) in anhydrous THF (100 mL) at ambient temperature was added methanesulfonic anhydride (1.24 g, 7.13 mmol). After 1 h, the reaction mixture was divided into two equal portions; to one of these portions was added bis(2-methoxyethyl)amine (6 mL). The mixture was stirred for 72 h, evaporated to dryness and the residue extracted with ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4), filtered and evaporated to a residue which was purified by column chromatography (silica, 20-30% ethyl acetate/hexane) to give an oil (0.71 g) which solidified upon standing: mp 75°-77° C.

Workup

  1. customevaporated to dryness
  2. extractionthe residue extracted with ethyl acetate (2×100 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to a residue which
  6. customwas purified by column chromatography (silica, 20-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5c385ab44b184238ab3e5f53550ba0d5
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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