1-[Bis(4-chlorophenyl)methyl]azetidin-3-ol → HCID 178527246, compound

HRID 277129Notes

Reaction equation

HRID 277129 reaction equation
[S:1]1[CH:5]=[N:4][N:3]=[C:2]1[CH2:6][NH:7][SH:8](=[O:10])=[O:9].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[N:19]2[CH2:22][CH:21](O)[CH2:20]2)=[CH:14][CH:13]=1>>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([CH:18]([C:15]2[CH:14]=[CH:13][C:12]([Cl:11])=[CH:17][CH:16]=2)[N:19]2[CH2:22][CH:21]([N:7]([CH2:6][C:2]3[S:1][CH:5]=[N:4][N:3]=3)[SH:8](=[O:10])=[O:9])[CH2:20]2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 218966141-[Bis(4-chlorophenyl)methyl]azetidin-3-olHCID 178527245HCID 178527245, compound

Product 1

HCID 178527246HCID 178527246, compoundYield 15.3%

Procedure

N-{1-[Bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(1,2,3,4-thiadiazol-2-yl)methylsulfonamide may be prepared by carrying out the procedure as described in Example 13 (method 2), from 0.10 g of N-(1,3,4-thiadiazol-2-yl)methylsulfonamide and 0.215 g of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ol. After chromatography on a silica gel column (particle size 0.06-0.04 mm, height 25 cm, diameter 1 cm), eluting under an argon pressure of 0.8 bar with an ethyl acetate/cyclohexane 20/80 and then 40/60 by volume mixture and collecting 60-cm3 fractions, fractions 26 to 31 are combined and concentrated to dryness under reduced pressure (2.7 kPa). After crystallization from dissopropyl ether, filtration and drying, 40 mg of N-{1-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-N-(1,3,4-thiadiazol-2-yl)methylsulfonamide are obtained in the form of a white solid [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 3.01 (s:3H); 3.09 (split t, J=7 and 1.5 Hz:2H); 3.70 (split t, J=7 and 1.5 Hz:2H); 4.28 (s:1H); 4.76 (mt:1H); from 7.20 to 7.35 (mt:8H); 9.01 (s:1H)].

Workup

  1. washAfter chromatography on a silica gel column (particle size 0.06-0.04 mm, height 25 cm, diameter 1 cm), eluting under an argon pressure of 0.8 bar with an ethyl acetate/cyclohexane 20/80
  2. custom40/60 by volume mixture and collecting 60-cm3 fractions, fractions 26 to 31
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customAfter crystallization
  5. filtrationfrom dissopropyl ether, filtration
  6. customdrying

Sources & evidence

ORD record
ord-b980d348769e45e4b63682128c483352
Source dataset
uspto-grants-2002_03
Patent number
US06355631B1

Reaction notes

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