Diisopropylethylamine → HCID 51035768, compound

HRID 480586Notes

Reaction equation

HRID 480586 reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.Cl[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[CH:28]=2)[N:23]=[CH:22][N:21]=1>C(Cl)Cl>[C:1]1([C@H:7]([NH:9][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6431891-Phenethylamine, (+)-HCID 113562574-Chloro-6-nitroquinazoline

Product 1

HCID 51035768HCID 51035768, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 6.40 ml of (R)-(1-phenylethyl)amine and 8.70 ml of diisopropylethylamine in 30 ml methylene chloride is added dropwise to 9.00 g of 4-chloro-6-nitroquinazoline in 70 ml methylene chloride while cooling with an ice bath. The mixture is allowed to come up to ambient temperature, then it is stirred for about another 48 hours. For working up, the reaction mixture is washed with water, 10% citric acid, and again with water. The organic phase is dried over magnesium sulfate and concentrated by evaporation. The solid evaporation residue is stirred with about 100 ml methanol, suction filtered, and washed with a little methanol. Yield: 8.44 g (67% of theory); Rf value: 0.33 (silica gel, cyclohexane/ethyl acetate=1:1); mass spectrum (ESI−): m/z=293 [M−H]−.

Workup

  1. temperaturewhile cooling with an ice bath
  2. customto come up to ambient temperature
  3. washthe reaction mixture is washed with water, 10% citric acid
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe solid evaporation residue
  7. stirringis stirred with about 100 ml methanol, suction
  8. filtrationfiltered
  9. washwashed with a little methanol

Sources & evidence

ORD record
ord-1378a315e5f345c99f92e785c6c0ce01
Source dataset
uspto-grants-2003_11
Patent number
US06653305B2

Reaction notes

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