Hydrochloric Acid → 2-Chloro-4-{1-[5-(3,4-dichlorophenyl)-4-hydroxythiophen-3-yl]ethylidenehydrazinocarbonyl}-N-(2-hydroxyethyl)benzamide

HRID 2425951Notes

Reaction equation

HRID 2425951 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([C:15]([CH3:17])=O)[C:13]=2[OH:14])[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:18][C:19]1[CH:30]=[C:29]([C:31]([NH:33][NH2:34])=[O:32])[CH:28]=[CH:27][C:20]=1[C:21]([NH:23][CH2:24][CH2:25][OH:26])=[O:22].Cl.O>CN(C)C=O>[Cl:18][C:19]1[CH:30]=[C:29]([C:31]([NH:33][N:34]=[C:15]([C:12]2[C:13]([OH:14])=[C:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[S:10][CH:11]=2)[CH3:17])=[O:32])[CH:28]=[CH:27][C:20]=1[C:21]([NH:23][CH2:24][CH2:25][OH:26])=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 442072882-(3,4-Dichlorophenyl)-3-hydroxy-4-(methylcarbonyl)thiopheneHCID 576880942-Chloro-4-(hydrazinecarbonyl)-N-(2-hydroxyethyl)benzamide2×

Product 1

HCID 765934662-Chloro-4-{1-[5-(3,4-dichlorophenyl)-4-hydroxythiophen-3-yl]ethylidenehydrazinocarbonyl}-N-(2-hydroxyethyl)benzamideYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-(3,4-dichlorophenyl)-3-hydroxy-4-methylcarbonylthiophene (40 mg, 0.14 mmol) and 2-chloro-4-hydrazinocarbonyl-N-(2-hydroxyethyl)benzamide (43 mg, 0.17 mmol) prepared in Reference Synthetic Example 8 in dimethylformamide (0.7 mL), concentrated hydrochloric acid (12 μL, 0.14 mmol) was added at room temperature, and the resulting mixture was stirred at room temperature for 1 day and stirred with 2-chloro-4-hydrazinocarbonyl-N-(2-hydroxyethyl)benzamide (18 mg, 0.07 mmol) for 1 day. After addition of water, the resulting crystals were recovered by filtration and dried. Chloroform was added, and the resulting crystals were recovered by filtration to give the desired product (yield 83%).

Workup

  1. filtrationthe resulting crystals were recovered by filtration
  2. customdried
  3. additionChloroform was added
  4. filtrationthe resulting crystals were recovered by filtration

Sources & evidence

ORD record
ord-5af452a24f5643a188689665190bdd8c
Source dataset
uspto-grants-2011_06
Patent number
US07968542B2

Reaction notes

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