Water → HCID 16075319, compound

HRID 1795117Notes

Reaction equation

HRID 1795117 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.[N:12](=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])\[NH2:13].Cl.C(N=C=NCCCN(C)C)C.O>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:13]/[N:12]=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=2)(=[O:24])=[O:23])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 158793-Chlorophenylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22185563HCID 22185563, compound

Product 1

HCID 16075319HCID 16075319, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31374DimethylacetamideSolvent

Procedure

A flask is charged with (3-chlorophenyl)acetic acid (0.34 mmol), 4-dimethylaminopyridine (0.66 mmol), a solution of N-{2-[(E)-hydrazonomethyl]phenyl}-4-(trifluoromethyl)benzenesulfonamide (0.33 mmol) in N,N-dimethylacetamide (1 mL), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.33 mmol). The reaction is stirred at room temperature for 18 hours. The reaction is worked up either by adding water and obtaining a solid precipitate, or by evaporating the reaction mixture. The product is purified on silica gel with ethyl acetate-methylene chloride mixtures. Obtained a 60% yield of N-[2-((E)-{[(3-chlorophenyl)acetyl]hydrazono}methyl)phenyl]-4-(trifluoromethyl)benzenesulfonamide. 1H NMR (400 MHz, CDCl3)(mixture of geometric isomers) d 3.73&4.17(2s, 2H); 7.16 (m); 7.36 (m); 7.47 (s); 7.60m; 7.66 (m); 7.75 (m); 7.89 (s); 7.96 (m); 8.06 (m); 9.62 (bs); 10.80 (bs). ESI− for C22H17ClF3N3O3S: m/z =494 (M−H)−.

Workup

  1. customobtaining a solid precipitate
  2. customby evaporating the reaction mixture
  3. customThe product is purified on silica gel with ethyl acetate-methylene chloride mixtures

Sources & evidence

ORD record
ord-d6f3cb0f9b26463c9cb7114359be3560
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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