Acetic Acid → HCID 15430886, compound

HRID 2257694Notes

Reaction equation

HRID 2257694 reaction equation
[CH2:1]([S:8][C:9]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>[Fe].O>[NH2:19][C:18]1[C:9]([S:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 54046874HCID 54046874, compound

Product 1

HCID 15430886HCID 15430886, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

69.8 g of iron powder are added in portions to a mixture of 68.0 g (0.22 mol) of methyl 2-benzylmercapto-3-nitrobenzoate, 215 ml of glacial acetic acid and 480 ml of water. The reaction solution is then stirred at 50°-60° C. for 3 h. The solid is separated off by filtration and then the mother liquor is washed with water and salt and subsequently dried over MgSO4. After concentration of the solution under reduced pressure, 47.1 g of a yellow oil (77%) are obtained; 1H NMR (CDCl3, 80 MHz): δ=3.8 (s, 3H, OCH3), 3.9 (s, 2H, SCH2Ph), 5.9 (s, 2H, NH2), 6.6-7.3 (m, 8H, Harom.).

Workup

  1. customThe solid is separated off by filtration
  2. washthe mother liquor is washed with water and salt
  3. dry with materialsubsequently dried over MgSO4

Sources & evidence

ORD record
ord-0fe56c9669a4426a96890a06416c949d
Source dataset
uspto-grants-1997_08
Patent number
US05658854

Reaction notes

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