Chloroacetyl chloride → HCID 20093932, compound

HRID 273806Notes

Reaction equation

HRID 273806 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[CH3:6][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].C(=O)([O-])O.[Na+]>C(OCC)C.O1CCCC1.N1C=CC=CC=1>[CH3:6][C:7]1[C:8]2[C:14]3[N:18]([CH:17]=[CH:16][N:15]=3)[C:3](=[O:4])[NH:10][C:9]=2[CH:11]=[CH:12][CH:13]=1.[CH3:6][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 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 20094140HCID 20094140, compound

Product 2

HCID 20093932HCID 20093932, compoundHCID 20094047HCID 20094047, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7. A solution of 8.25 ml of chloroacetyl chloride in 25 ml of diethyl ether is added dropwise at 0° C. within 15 min. to a solution of 11.5 g of 3-methyl-2-(1H-2-imidazolyl)aniline in 0.35 l of tetrahydrofuran and 21 ml of pyridine. The reaction mixture is stirred at 0° C. for 1 h, and then poured into saturated aqueous sodium hydrogen carbonate solution. The mixture is extracted three times with chloroform. The organic extracts are evaporated in a vacuum. The residue (13 g) is dissolved in 300 ml of dioxan and treated with 200 ml of 1N aqueous sodium hydroxide solution. The mixture is stirred at room temperature for 16 h., then adjusted to pH 6 with hydrochloric acid and evaporated in a vacuum. The residue is suspended in absolute ethanol and the insoluble inorganic salt is filtered off. The filtrate is evaporated in a vacuum, the residue is dissolved in trifluoroacetic acid and stirred at room temperature for 16 h. The reaction mixture is evaporated in a vacuum and the residue is partitioned between chloroform and saturated aqueous sodium hydrogen carbonate solution. The organic phases are evaporated in a vacuum. The residue is chromatographed over a column of 500 g of silica gel. Elution with ethyl acetate gives in succession 1.4g of 10-methylimidazo[1,2-c]quinazolin-5(6H)-one (m.p. 308°-310° C.) and 9.0 g 11-methyl-5H-imidazo[1,2-d][1,4]benzodiazepin-6(7H)-one of m.p. 188°-189° C.

Workup

  1. extractionThe mixture is extracted three times with chloroform
  2. customThe organic extracts are evaporated in a vacuum
  3. dissolutionThe residue (13 g) is dissolved in 300 ml of dioxan
  4. additiontreated with 200 ml of 1N aqueous sodium hydroxide solution
  5. stirringThe mixture is stirred at room temperature for 16 h.
  6. customevaporated in a vacuum
  7. filtrationthe insoluble inorganic salt is filtered off
  8. customThe filtrate is evaporated in a vacuum
  9. dissolutionthe residue is dissolved in trifluoroacetic acid
  10. stirringstirred at room temperature for 16 h
  11. customThe reaction mixture is evaporated in a vacuum
  12. customthe residue is partitioned between chloroform and saturated aqueous sodium hydrogen carbonate solution
  13. customThe organic phases are evaporated in a vacuum
  14. customThe residue is chromatographed over a column of 500 g of silica gel
  15. washElution with ethyl acetate

Sources & evidence

ORD record
ord-05c7faab9ce242e7b088f029d38fadad
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

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