Water → HCID 13579372, compound

HRID 1589082Notes

Reaction equation

HRID 1589082 reaction equation
O.[CH3:2][O:3][C:4]([C:6]1[CH:7]=[C:8]([CH:12]([C:15]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:16])[C:13]#[N:14])[CH:9]=[CH:10][CH:11]=1)=[O:5].BrBr.C(=O)(O)[O-:27].[Na+]>C(Cl)Cl>[C:18]1([CH:17]2[C:15](=[O:16])[C:12]([C:8]3[CH:9]=[CH:10][CH:11]=[C:6]([C:4]([O:3][CH3:2])=[O:5])[CH:7]=3)=[C:13]([NH2:14])[O:27]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408Bromine2×HCID 516892Sodium BicarbonateHCID 13579371HCID 13579371, compound

Product 1

HCID 13579372HCID 13579372, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In this example 0.4 g of water was admixed with 6.5 g of (3-methoxycarbonylphenyl)-benzylcarbonyl-acetonitrile in about 40 ml of methylene chloride at room temperature. 1.1 ml of bromine in about 10 ml of methylene chloride was added dropwise at room temperature. After addition of the bromine, the reaction mixture was mixed with saturated aqueous sodium bicarbonate and stirred for about 1/2 hour at room temperature, resulting in a two-phase liquid mixture. The phases were separated. The aqueous phase was extracted three times with methylene chloride. The combined extracts and methylene chloride phase were washed twice with saturated aqueous sodium bicarbonate, dried over magnesium sulfate and concentrated by evaporation affording an oily residue. The residue was triturated with a mixture of ethyl ether and petroleum ethers affording 5.0 g of the title compound as a solid.

Workup

  1. customresulting in a two-phase liquid mixture
  2. customThe phases were separated
  3. extractionThe aqueous phase was extracted three times with methylene chloride
  4. washThe combined extracts and methylene chloride phase were washed twice with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. customaffording an oily residue
  8. customThe residue was triturated with a mixture of ethyl ether and petroleum ethers affording 5.0 g of the title compound as a solid

Sources & evidence

ORD record
ord-92d7da319cea4e848489f384b8043f9d
Source dataset
uspto-grants-1986_02
Patent number
US04568377

Reaction notes

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