Triethylamine → HCID 19434018, compound

HRID 1736032Notes

Reaction equation

HRID 1736032 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[S:11](Cl)(=[O:13])=[O:12].C1OC(C2C=CSC=2)OC1.[NH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30].C(N(CC)CC)C>C(=O)(O)[O-].[Na+]>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[S:11]([NH:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 258684-Amino-1-butanolHCID 3156302-(3-Thienyl)-1,3-dioxolaneHCID 105389153-(1,3-dioxolan-2-yl)thiophene-2-sulfonyl Chloride

Product 1

HCID 19434018HCID 19434018, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 3-(1,3-dioxolan-2-yl)-thiophene-2-sulfonyl chloride, prepared from thiophene-3-carboxaldehyde ethylene acetal (20.0 g, 128 mmol) as described in Example 6, Step A, was combined with 4-amino-1-butanol (17.1 g, 192 mmol) and triethylamine (15 g, 148 mmol). The reaction was stirred for 1 h, a saturated aqueous solution of sodium bicarbonate (200 mL) was added and this mixture was stirred for 1 h. The organic layer was separated, dried (MgSO4), and evaporated to a residue which was purified by column chromatography (silica, 50% ethyl acetate/hexane to ethyl acetate, gradient) to give an oil (26.45 g, 62%).

Workup

  1. stirringthis mixture was stirred for 1 h
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. customevaporated to a residue which
  5. customwas purified by column chromatography (silica, 50% ethyl acetate/hexane to ethyl acetate, gradient)

Sources & evidence

ORD record
ord-d9df0f99478a4f689971c89dd8c8370d
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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