Bis(2-Methoxyethyl)amine → HCID 19434107, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14]([CH2:15]O)=[CH:13][C:12]3[CH:17]=[CH:18][S:19][C:11]=3[S:10]2(=[O:21])=[O:20])=[CH:5][CH:4]=1.C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[CH3:38][O:39][CH2:40][CH2:41][NH:42][CH2:43][CH2:44][O:45][CH3:46].C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:38][O:39][CH2:40][CH2:41][N:42]([CH2:15][C:14]1[N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[S:10](=[O:21])(=[O:20])[C:11]2[S:19][CH:18]=[CH:17][C:12]=2[CH:13]=1)[CH2:43][CH2:44][O:45][CH3:46]Participants
7
Procedure
To a solution of the product of Step D (1.19 g, 3.68 mmol) and triethylamine (1.24 g, 12.3 mmol) in anhydrous THF (50 mL) was added methanesulfonic anhydride (1.07 g, 6.13 mmol). After 30 min, bis(2-methoxyethyl)amine (3 mL) was added and stirring continued for 18 h at ambient temperature. The reaction mixture was heated at reflux temperature for 1 h, cooled, poured into a saturated solution of sodium bicarbonate (100 mL) and this mixture was extracted with ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, 40% ethyl acetate/hexane) to give a viscous oil (1.16 g, 72%).
Workup
- waitcontinued for 18 h at ambient temperature
- temperatureThe reaction mixture was heated
- temperatureat reflux temperature for 1 h
- temperaturecooled
- extractionthis mixture was extracted with ethyl acetate (2×100 mL)
- dry with materialThe combined extracts were dried (MgSO4)
- customevaporated to a residue which
- customwas purified by column chromatography (silica, 40% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-39d2a68bec7b4f77a0a41212220d6c5f
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05538966
Reaction notes
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