Dimethyl Sulfoxide → 1-[Bis(thien-2-yl)methyl]azetidin-3-one

HRID 25191Notes

Reaction equation

HRID 25191 reaction equation
N1CC(=O)C1.[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[N:12]1[CH2:15][CH:14]([OH:16])[CH2:13]1.CS(C)=O.C(Cl)(=O)C(Cl)=O>ClCCl.C(N(CC)CC)C>[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH:11]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[N:12]1[CH2:13][C:14](=[O:16])[CH2:15]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 1516505Azetidin-3-oneHCID 225067841-[Bis(thien-2-yl)methyl]azetidin-3-ol

Product 1

HCID 225067061-[Bis(thien-2-yl)methyl]azetidin-3-oneYield 80.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1-[Bis-thien-2-yl)methyl]azetidin-3-one may be prepared by carrying out the operation as described in Example 73, starting with 4 g of 1-[bis(thien-2-yl)methyl]azetidin-3-ol, 2.6 cm3 of dimethyl sulfoxide, 7.7 cm3 of triethylamine, 7.7 cm3 of oxalyl chloride, and 100 cm3 of dichloromethane. The residue obtained is purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 3 cm, height 30 cm) with, as eluent, a mixture of cyclohexane/ethyl acetate (1/1 by volume). The fractions obtained are evaporated to dryness under reduced pressure (2.7 Kpa). 3.2 g of 1-[bis(thien-2-yl)methyl]azetidin-3-one are obtained in the form of cream-colored crystals melting at 70° C.

Workup

  1. customThe residue obtained
  2. customis purified by chromatography on a silica gel column (particle size 0.04-0.06 mm, diameter 3 cm, height 30 cm) with, as eluent
  3. additiona mixture of cyclohexane/ethyl acetate (1/1 by volume)
  4. customThe fractions obtained
  5. customare evaporated to dryness under reduced pressure (2.7 Kpa)

Sources & evidence

ORD record
ord-8f5203b24ec644d291546c522326bf2e
Source dataset
uspto-grants-2005_02
Patent number
US06858603B2

Reaction notes

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