Hydrochloric Acid → HCID 72360074, compound

HRID 1881640Notes

Reaction equation

HRID 1881640 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][CH:14]=[C:13]([C:16](=[N:18][NH:19][C:20]([NH:22][C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[C:25]([Cl:33])[CH:24]=3)=[S:21])[CH3:17])[C:12]=2[OH:34])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C(O)(C)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][CH:14]=[C:13]([C:16](=[N:18][NH:19][C:20]([NH:22][C:23]3[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[C:25]([Cl:33])[CH:24]=3)=[S:21])[CH3:17])[C:12]=2[OH:34])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 72360096HCID 72360096, compound

Product 1

HCID 72360074HCID 72360074, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Methyl 4-{[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonothioyl]amino}-2-chlorobenzoate (100 mg, 0.19 mmol) synthesized in Synthetic Example 100 was dissolved in isopropyl alcohol (1.9 ml), and 0.2 M sodium hydroxide aqueous solution (2.1 ml, 0.42 mmol) was added thereto, following by stirring overnight at room temperature, then at 45° C. for 1 day. Then 0.2 M sodium hydroxide aqueous solution (1.1 ml, 0.22 mmol) was added thereto, following by stirring at 45° C. for 5.5 hours. After completion of the stirring, 1 M hydrochloric acid (0.64 ml, 0.64 mmol) was added. The precipitated solid was filtered, and purified with a silica gel plate (chloroform/methanol=9/1) to obtain the desired product as a yellow solid (24 mg, yield 25%).

Workup

  1. waitat 45° C. for 1 day
  2. stirringby stirring at 45° C. for 5.5 hours
  3. filtrationThe precipitated solid was filtered
  4. custompurified with a silica gel plate (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-4fae06b43e6d4b869c94b66742a7a891
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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