Triethylamine → HCID 54426173, compound

HRID 362291Notes

Reaction equation

HRID 362291 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=1)[CH3:11].C(N(CC)CC)C>CS(C)=O.ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH:22]=[O:23])=[CH:19][CH:20]=1)[CH3:11]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 18794842HCID 18794842, compound

Product 1

HCID 54426173HCID 54426173, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of pyridine-sulphur trioxide complex (1.53 g) in dimethylsulphoxide (5 mL) was added to a stirred, ice cooled mixture of 2-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]ethanol (1.00 g), triethylamine (2.25 mL) and dichloromethane (30 mL) under a nitrogen atmosphere. The mixture was stirred at 0° C. for 10 minutes, then at room temperature for 5 hours before being diluted with dichloromethane (100 mL) and washed with water (2×100 mL), hydrochloric acid (0.5M; 100 mL), water (2×100 mL) and brine (100 mL), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel with 5% ethyl acetate in dichloromethane as solvent to afford the title compound, a gum.

Workup

  1. temperaturecooled
  2. washwashed with water (2×100 mL), hydrochloric acid (0.5M; 100 mL), water (2×100 mL) and brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel with 5% ethyl acetate in dichloromethane as solvent

Sources & evidence

ORD record
ord-3b3a6f6b44c447b0982d74d9fc545f5e
Source dataset
uspto-grants-1999_02
Patent number
US05869495

Reaction notes

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