Isopropanol → HCID 22731361, compound

HRID 2085483Notes

Reaction equation

HRID 2085483 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:13]=2[C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=1)=[O:4].C(O)(C)C.[Cl-].[NH4+]>[Fe].C(Cl)(Cl)Cl>[NH2:22][C:19]1[CH:20]=[CH:21][C:12]([S:11][C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 25517Ammonium ChlorideHCID 22731366HCID 22731366, compound

Product 1

HCID 22731361HCID 22731361, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 1.09 g of methyl 2-(4-methoxycarbonylphenylthio)-5-nitrobenzoate obtained in the same procedures as described in Reaction Scheme (24) of Example 1 and 1.75 g of iron powder, were added 3 ml of isopropyl alcohol and an aqueous solution of ammonium chloride (0.05 g of ammonium chloride and 0.95 ml of water). The mixture was stirred for 10 minutes at 85° C. Chloroform was added to the reaction mixture. The mixture was filtered with celite, and was subsequently washed with chloroform. A mixture of the filtrate and the washing was washed with saturated brine, and was subsequently dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, 0.996 g of methyl 5-amino-2-(4-methoxycarbonylphenylthio)benzoate (yellow viscous substance) was obtained (Reaction Scheme (31) described below).

Workup

  1. customobtained in the same procedures
  2. filtrationThe mixture was filtered with celite
  3. washwas subsequently washed with chloroform
  4. additionA mixture of the filtrate
  5. washthe washing was washed with saturated brine
  6. dry with materialwas subsequently dried over anhydrous magnesium sulfate
  7. customAfter the solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-305b1a1d3d2d423cbd94c9fe00fae7dd
Source dataset
uspto-grants-2004_04
Patent number
US06720424B1

Reaction notes

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