Hydrazine hydrate (1:1) → 2-(Chloromethyl)-4-hydrazino-6-methylquinazoline

HRID 273796Notes

Reaction equation

HRID 273796 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([CH2:13][Cl:14])[N:3]=1.O.[NH2:16][NH2:17].C(=O)([O-])O.[Na+]>O1CCCC1.O>[Cl:14][CH2:13][C:4]1[N:3]=[C:2]([NH:16][NH2:17])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=1

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 200939274-Chloro-2-(chloromethyl)-6-methylquinazoline

Product 1

HCID 200940532-(Chloromethyl)-4-hydrazino-6-methylquinazoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

3. 63.5 g of 4-chloro-2-(chloromethyl)-6-methylquinazoline are dissolved in 630 ml of absolute tetrahydrofuran at room temperature and then cooled to 10° C. 27.2 ml of hydrazine hydrate are added dropwise thereto within 8 min., whereby a solution results and the temperature rises to 15° C. The reaction mixture is stirred at 5° to 15° C. for 4 h. and then poured into a solution of 40 g of sodium hydrogen carbonate in 5 l of water. The mixture is extracted five times with 1.5 l of dichloromethane each time. The combined organic phases are washed with water, dried and concentrated (T<40° C.) in a vacuum to a volume of 0.5 l. 0.5 l of ethyl acetate is added thereto and the dichloromethane is evaporated completely in a vacuum, whereby the product crystallizes out. The mixture is left to stand at -25° C. overnight and the crystals are filtered off, washed with diethyl ether and dried at room temperature in a vacuum. There are obtained 38 g of 2-(chloromethyl)-4-hydrazino-6-methylquinazoline of m.p. above 140° C. (dec.).

Workup

  1. customwhereby a solution results
  2. customrises to 15° C
  3. extractionThe mixture is extracted five times with 1.5 l of dichloromethane each time
  4. washThe combined organic phases are washed with water
  5. customdried
  6. concentrationconcentrated (T<40° C.) in a vacuum to a volume of 0.5 l
  7. addition0.5 l of ethyl acetate is added
  8. customthe dichloromethane is evaporated completely in a vacuum, whereby the product
  9. customcrystallizes out
  10. waitThe mixture is left
  11. waitto stand at -25° C. overnight
  12. filtrationthe crystals are filtered off
  13. washwashed with diethyl ether
  14. customdried at room temperature in a vacuum

Sources & evidence

ORD record
ord-f1c4e45aebbc4ecdaa6450d5cf19dcfd
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

Loading…