Water → HCID 20094113, compound

HRID 273802Notes

Reaction equation

HRID 273802 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[Br:6][C:7]1[C:8]([C:14]2[NH:15][CH:16]=[CH:17][N:18]=2)=[C:9]([CH:11]=[CH:12][CH:13]=1)[NH2:10].[OH-].[Na+].O>C(OCC)C.O1CCOCC1.N1C=CC=CC=1>[Br:6][C:7]1[C:8]2[C:14]3[N:18]([CH:17]=[CH:16][N:15]=3)[CH2:2][C:3](=[O:4])[NH:10][C:9]=2[CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chloride2×HCID 14798Sodium HydroxideHCID 20094043HCID 20094043, compound

Product 1

HCID 20094113HCID 20094113, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
5 °C

Procedure

6. A solution of 2.4 ml of chloroacetyl chloride in 10 ml of diethyl ether is added dropwise at 5° C. within 15 min. to a solution of 6.0g of 3-bromo-2-(1H-2-imidazolyl)aniline in 150 ml of dioxan and 6.1 ml of pyridine. The mixture is stirred at 5° C. for 10 min. and then a solution of 0.25 ml of chloroacetyl chloride in 5 ml of diethyl ether is again added dropwise thereto. The mixture is stirred at 10° to 12° C. for a further 30 min. and then treated within 5 min. with a mixture of 75 ml of aqueous 1N sodium hydroxide solution and 150 ml of dioxan. The mixture is stirred at room temperature for 45 min. and then poured into 1 l of water. The mixture is extracted four times with chloroform. The chloroform extracts are evaporated in a vacuum. The oily residue is crystallized from dichloromethane/diethyl ether. 0.99g of 11-bromo-5H-imidazo[1,2-d][1,4]benzodiazepin-6(7H)-one of m.p. 234°-235° C. is obtained. The aqueous phase is evaporated in a vacuum. The residue is taken up several times in ethanol and toluene and evaporated in a vacuum each time. The residue is dissolved in 150 ml of trifluoroacetic acid and left to stand at room temperature for 16 h. The reaction mixture is evaporated in a vacuum and the residue is partitioned between saturated aqueous sodium hydrogen carbonate solution and chloroform. The organic extracts are evaporated in a vacuum and the residue is crystallized from dichloromethane/diethyl ether. There are obtained a further 3.37 of 11-bromo-5H-imidazo[1,2-d][1,4]benzodiazepin-6(7H)-one.

Workup

  1. stirringThe mixture is stirred at 10° to 12° C. for a further 30 min.
  2. stirringThe mixture is stirred at room temperature for 45 min.
  3. extractionThe mixture is extracted four times with chloroform
  4. customThe chloroform extracts are evaporated in a vacuum
  5. customThe oily residue is crystallized from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-3d0c400f39b0481397ea4ba908526b81
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

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