HCID 22506811, compound → 1-[Bis(4-chlorophenyl)methyl]-3-[(3-methylaminophenyl)(methylsulfonyl)methylene]azetidine

HRID 25195Notes

Reaction equation

HRID 25195 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[N:9]2[CH2:12][C:11](=[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N:24](C(OC(C)(C)C)=O)[CH3:25])[CH:19]=3)[S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10]2)=[CH:4][CH:3]=1>O1CCOCC1>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]2[CH2:12][C:11](=[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][CH3:25])[CH:19]=3)[S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10]2)=[CH:34][CH:35]=1

Participants

3

Reactant 1

HCID 22506811HCID 22506811, compound

Product 1

HCID 219550931-[Bis(4-chlorophenyl)methyl]-3-[(3-methylaminophenyl)(methylsulfonyl)methylene]azetidineYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

2.7 g of 1-[bis(4-chlorophenyl)methyl]-3-{[3-(N-tertbutyloxycarbonyl-N-methylamino)phenyl](methylsulfonyl)methylene}azetidine in 30 cm3 of dioxane and 30 cm3 of a 4.7 N solution of hydrochloric dioxane are stirred for 20 hours. The reaction medium is evaporated to dryness under reduced pressure (2.7 kpa), taken up in 50 cm3 of water and 50 cm3 of ethyl acetate, stirred and neutralized carefully with a saturated aqueous sodium bicarbonate solution. The organic phase is separated, dried over magnesium sulfate, treated with animal charcoal and then concentrated under reduced pressure (2.7 kpa) to a volume of about 25 cm3, then filtered, concentrated to dryness under reduced pressure. 1.3 g of 1-[bis(4-chlorophenyl)methyl]-3-[(3-methylaminophenyl)(methylsulfonyl)methylene]azetidine are obtained in the form of white crystals melting at 228° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 2.65 (3H, s, J=6 Hz, NCH3), 2.95 (3H, s, SCH3), 3.80 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.80 (1H, s, NCH), 5.85 (1H, q, J=6 Hz, NH), 6.55 (3H, m, 3 CH arom.), 7.15 (1H, t, J=7 Hz, CH arom.), 7.40 (4H, d, J=7 Hz, 4CH arom.), 7.50 (4H, m, 4CH arom.)].

Workup

  1. customThe reaction medium is evaporated to dryness under reduced pressure (2.7 kpa)
  2. customThe organic phase is separated
  3. dry with materialdried over magnesium sulfate
  4. additiontreated with animal charcoal
  5. concentrationconcentrated under reduced pressure (2.7 kpa) to a volume of about 25 cm3
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-cda704ac74714b7bbee74105cf41b035
Source dataset
uspto-grants-2005_02
Patent number
US06858603B2

Reaction notes

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