18-Crown-6 → HCID 20562372, compound

HRID 848548Notes

Reaction equation

HRID 848548 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]2[N:17]([CH3:18])[C:16](=[O:19])[CH2:15][N:14]=[C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:12]=2[C:27]=1[Cl:28])=[O:6].[C:29]([O-:32])(=[O:31])[CH3:30].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[C:29]([O:32][CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]2[N:17]([CH3:18])[C:16](=[O:19])[CH2:15][N:14]=[C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:12]=2[C:27]=1[Cl:28])=[O:6])(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 517044Potassium AcetateHCID 20562369HCID 20562369, compound

Product 1

HCID 20562372HCID 20562372, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.7 g 1-(2-chloroethyl)-3-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]urea dissolved in 100 ml of acetonitrile are treated with 1.83 g of potassium acetate and 4.21 g of 18-crown-6. The mixture is then stirred at room temperature for 5 days, concentrated, treated with water/methylene chloride and the aqueous solution is extracted several times with methylene chloride. The organic solution is dried with sodium sulphate, filtered and concentrated. The residue is purified on a 350 g silica gel column using ethyl acetate as the eluting agent and crystallised from ethanol/ether. There is obtained 2-[3-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]ethyl acetate.

Workup

  1. concentrationconcentrated
  2. additiontreated with water/methylene chloride
  3. extractionthe aqueous solution is extracted several times with methylene chloride
  4. dry with materialThe organic solution is dried with sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified on a 350 g silica gel column
  8. customcrystallised from ethanol/ether

Sources & evidence

ORD record
ord-8decbb0a85144a1a84e0a14db4719ebc
Source dataset
uspto-grants-1981_10
Patent number
US04296031

Reaction notes

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