Hydrochloric Acid → HCID 68806941, compound

HRID 855789Notes

Reaction equation

HRID 855789 reaction equation
[Cl:1][C:2]1[CH:28]=[C:27]([F:29])[C:26]([F:30])=[CH:25][C:3]=1[C:4]([NH:6][C:7](=[O:24])[NH:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[O:21])=[O:5].Cl>[Zn].C(O)(=O)C>[NH2:15][C:13]1[CH:12]=[CH:11][C:10]([CH:18]=[CH:19][C:20]([O:22][CH3:23])=[O:21])=[C:9]([NH:8][C:7]([NH:6][C:4](=[O:5])[C:3]2[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:2]=2[Cl:1])=[O:24])[CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68806749HCID 68806749, compound

Product 1

HCID 68806941HCID 68806941, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

8.5 g (19.3 mmol) of methyl 3-{2-[3-(2-chloro-4,5-difluorobenzoyl)ureido]-4-nitro-phenyl}acrylate were suspended in 60 ml of a mixture of glacial acetic acid and concentrated hydrochloric acid (10:1) and heated to 70° C. Then 8.85 g (135.3 mmol) of zinc powder were added. After 30 minutes, the mixture was cooled, the solid was filtered off with suction, and the filtrate was concentrated. The residue was taken up in ethyl acetate and washed with a 10% strength sodium bicarbonate solution. The organic phase was dried and concentrated. 7.9 g (100%) of the desired product were obtained.

Workup

  1. temperaturethe mixture was cooled
  2. filtrationthe solid was filtered off with suction
  3. concentrationthe filtrate was concentrated
  4. washwashed with a 10% strength sodium bicarbonate solution
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-99d6fb7ea3944e849d2a776e5b506092
Source dataset
uspto-grants-2007_08
Patent number
US07262220B2

Reaction notes

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