Chloroacetyl chloride → HCID 20093956, compound

HRID 273787Notes

Reaction equation

HRID 273787 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[NH2:8])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:19][CH2:20][C:21](Cl)=O>O1CCCC1.C(OCC)C>[Cl:19][CH2:20][C:21]1[N:2]2[N:1]=[CH:5][CH:4]=[C:3]2[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 11430Potassium CarbonateHCID 178507484HCID 178507484, compound

Product 1

HCID 20093956HCID 20093956, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

2.1. 8.6 g of 2-(1H-pyrazol-3-yl)aniline are dissolved in 800 ml of tetrahydrofuran. 75.3 g of potassium carbonate are added thereto, the mixture is cooled to 5° C. and then a solution of 6.7 ml of chloroacetyl chloride in 40 ml of diethyl ether is added dropwise thereto within 10 min. The mixture is stirred at 5° C. for 30 min. and then a solution of 0.67 ml of chloroacetyl chloride in 5 ml of diethyl ether is again added dropwise thereto. The mixture is stirred for a further 15 min. and then the insoluble constituent is filtered off, The filtrate is evaporated in a vacuum. The residue is partitioned between saturated aqueous sodium hydrogen carbonate solution and dichloromethane. The aqueous phase is extracted several times with dichloromethane. The organic extracts are dried and evaporated in a vacuum. The residue is taken up in 560 ml of a 0.41N solution of hydrogen chloride in dioxan and stirred at 90° C. for 1 h. The solution is evaporated in a vacuum and the residue is partitioned between saturated aqueous sodium hydrogen carbonate solution and dichloromethane. The dichloromethane extract is evaporated in a vacuum. 11.4 g of 5-(chloromethyl)-pyrazolo[1,5-c]quinazoline are obtained. The m.p. is 135°-136° C. after recrystallization from diisopropyl ether.

Workup

  1. stirringThe mixture is stirred for a further 15 min.
  2. filtrationthe insoluble constituent is filtered off
  3. customThe filtrate is evaporated in a vacuum
  4. customThe residue is partitioned between saturated aqueous sodium hydrogen carbonate solution and dichloromethane
  5. extractionThe aqueous phase is extracted several times with dichloromethane
  6. customThe organic extracts are dried
  7. customevaporated in a vacuum
  8. stirringstirred at 90° C. for 1 h
  9. customThe solution is evaporated in a vacuum
  10. customthe residue is partitioned between saturated aqueous sodium hydrogen carbonate solution and dichloromethane
  11. extractionThe dichloromethane extract
  12. customis evaporated in a vacuum

Sources & evidence

ORD record
ord-1cfeb463f2b843bbb33c53728756049c
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

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