Methanol → HCID 178486607, compound

HRID 1633570Notes

Reaction equation

HRID 1633570 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Br:11])[CH:10]=1)[NH:7][C:6](=[O:12])[C:5]2=O.C([C:18]1[CH:19]=[C:20]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:21]2[O:25][C:24](=[O:26])[CH2:23][C:22]=2[CH:27]=1)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:43][OH:44]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Br:11])[CH:10]=1)[NH:7][C:6](=[O:12])[C:5]2=[C:23]1[C:22]2[CH:27]=[C:18]([O:44][CH3:43])[CH:19]=[C:20]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:21]=2[O:25][C:24]1=[O:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 18099205,7-dibromoisatinHCID 5324643HCID 5324643, compound

Product 1

HCID 178486607HCID 178486607, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

7.6 g (0.025 mol) of 5,7-dibromoisatin, 6.15 g (0.025 mol) of 5,7-di-tert-butyl-3H-benzofuran-2-one and 0.5 g of p-toluenesulfonic acid are boiled in 25 ml of acetic acid under nitrogen for 21 hours. 40 ml of methanol are then added and the suspension obtained is cooled to 5° C. The solid then obtained is filtered off and the filter residue is washed with methanol and dried at 60° C. The yield is 10.7 g (80% of theory). Melting point: 303-314° C. C: calculated/found 49.73/49.46; H: calculated/found 3.38/3.45; N: calculated/found 2.76/2.73

Workup

  1. customthe suspension obtained
  2. customThe solid then obtained
  3. filtrationis filtered off
  4. washthe filter residue is washed with methanol
  5. customdried at 60° C

Sources & evidence

ORD record
ord-4231e7fd8dae404292584e5b9ed22bf0
Source dataset
uspto-grants-2003_01
Patent number
US06503937B1

Reaction notes

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