Hydrazine hydrate (1:1) → 2-(Chloromethyl)-4-hydrazinylquinazoline
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:12][Cl:13])[N:3]=1.O.[NH2:15][NH2:16]>O1CCCC1>[Cl:13][CH2:12][C:4]1[N:3]=[C:2]([NH:15][NH2:16])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2.1. 46.0g of 4-chloro-2-(chloromethyl)quinazoline are suspended in 600 ml of absolute tetrahydrofuran. The solution is cooled to 0° C. 23.0 ml of hydrazine hydrate are added dropwise within 5 min., whereby a solution results and the temperature rises to 15° to 20° C. The reaction mixture is stirred at room temperature for 4 h. and then evaporated in a vacuum. The residue is triturated with 0.5 l of dichloromethane and 1 l of a saturated aqueous sodium hydrogen carbonate solution and then filtered. The crystals are washed neutral with water and dried in a vacuum. 38 g of 2-(chloromethyl)-4-hydrazinoquinazoline are obtained. The dichloromethane phase of the filtrate is separated and the aqueous phase is extracted with dichloromethane. By evaporation of the organic phases, there are obtained a further 5.8 g of 2-(chloro-methyl)-4-hydrazinoquinazoline. In total there are obtained 43.8 g of 2-(chloromethyl)-4-hydrazino- quinazoline. M.p. 192° C. (dec.).
Workup
- customwhereby a solution results
- customrises to 15° to 20° C
- customevaporated in a vacuum
- customThe residue is triturated with 0.5 l of dichloromethane and 1 l of a saturated aqueous sodium hydrogen carbonate solution
- filtrationfiltered
- washThe crystals are washed neutral with water
- customdried in a vacuum
Sources & evidence
- ORD record
- ord-2367aed4d515405392644b40b71fed0f
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05387585
Reaction notes
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