p-(Methylsulphonyl)benzoic acid → Diisopropylcarbodiimide

HRID 413030Notes

Reaction equation

HRID 413030 reaction equation
CS(C1C=CC(C(O)=O)=CC=1)(=O)=O.O[C:15]1[C:23]2[N:22]=NN[C:19]=2C=CC=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([C:49]2[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=2)[N:32]2[CH2:35][CH:34]([NH:36]C(=O)C3C=CC(S(C)(=O)=O)=CC=3)[CH2:33]2)=[CH:27][CH:26]=1>CN(C)C=O.ClCCl>[CH:31]([N:32]=[C:33]=[N:22][CH:23]([CH3:19])[CH3:15])([CH3:49])[CH3:28].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([C:49]2[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=2)[N:32]2[CH2:33][CH:34]([NH2:36])[CH2:35]2)=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 77670p-(Methylsulphonyl)benzoic acidHCID 17751339HCID 17751339, compoundHCID 178418300HCID 178418300, compound

Product 2

HCID 12734DiisopropylcarbodiimideHCID 218965981-[Bis(4-chlorophenyl)methyl]azetidin-3-ylamine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

By carrying out the operation according to the procedure of Example 31, starting with 58.5 mg of 4-methylsulfonylbenzoic acid, 26.4 mg of hydroxybenzotriazole in solution in 0.5 cm3 of dimethylformamide, 0.0302 cm3 of diisopropylcarbodiimide, a solution of 30 mg of 1-[bis(4-chlorophenyl)methyl]azetidin-3-ylamine in 0.5 cm3 of anhydrous dichloromethane, and 3 cm3 of anhydrous dichloromethane, N-{l-[bis(4-chlorophenyl)methyl]azetidin-3-yl}-4-methylsulfonylbenzamide is obtained in the form of a white crystals [1H NMR spectrum (300 MHz, CDCl3, δ in ppm): 3.03 (mt: 2H) 3.09 (s: 3H); 3.61 (broad t, J=7.5 Hz: 2H); 4.35 (s: 1H); 4.73 (mt: 1H); 6.55 (broad d, J=7.5 Hz: 1H); from 7.20 to 7.35 (mt: 8H); 7.96 (d, J=8 Hz: 2H); 8.03 (d, J=8 Hz: 2H)].

Sources & evidence

ORD record
ord-7f9d1ae926ec4e528e431a293d7965d3
Source dataset
uspto-grants-2003_05
Patent number
US06566356B2

Reaction notes

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