Water → HCID 91398644, compound

HRID 1094932Notes

Reaction equation

HRID 1094932 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].[C:18]([O:22][C:23](=[O:37])[CH2:24][NH:25][C:26]([C:28]1[S:29][C:30]([C:33]([NH:35][NH2:36])=[O:34])=[CH:31][CH:32]=1)=[O:27])([CH3:21])([CH3:20])[CH3:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(O)(C)C>[C:18]([O:22][C:23](=[O:37])[CH2:24][NH:25][C:26]([C:28]1[S:29][C:30]([C:33]([NH:35][N:36]=[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:34])=[CH:31][CH:32]=1)=[O:27])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 442072882-(3,4-Dichlorophenyl)-3-hydroxy-4-(methylcarbonyl)thiopheneHCID 91507662HCID 91507662, compound

Product 1

HCID 91398644HCID 91398644, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-(3,4-Dichlorophenyl)-3-hydroxy-4-methylcarbonylthiophene (49 mg, 0.17 mmol) in isopropanol (2.0 mL) was heated with tert-butyl{[5-(hydrazinocarbonyl)thiophene-2-carbonyl]amino}acetate (44 mg, 0.15 mmol) prepared in Reference Synthetic Example 8 and 3 mg of p-toluenesulfonic acid monohydrate at 100° C. for 8 hours and allowed to cool to room temperature. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed with water, methanol and chloroform and dried to give 69 mg of the desired product (yield 83%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water, methanol and chloroform
  3. customdried

Sources & evidence

ORD record
ord-490fbee343c346418eb80f529529999a
Source dataset
uspto-grants-2012_03
Patent number
US08134013B2

Reaction notes

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