Methyl chloroformate → HCID 57313676, compound

HRID 1391045Notes

Reaction equation

HRID 1391045 reaction equation
Cl[C:2](OC)=[O:3].[NH2:6][CH2:7][C:8]1[C:14]([O:15][CH2:16][CH:17]([OH:31])[CH2:18][N:19]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10]>C(O)(C)C.O>[CH2:20]([N:19]([C:27]([CH3:28])([CH3:30])[CH3:29])[CH2:18][CH:17]([OH:31])[CH2:16][O:15][C:14]1[CH:13]=[CH:12][CH:11]=[C:9]2[C:8]=1[CH2:7][NH:6][C:2](=[O:3])[NH:10]2)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 57124165HCID 57124165, compound

Product 1

HCID 57313676HCID 57313676, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

5.3 g of methyl chloroformate are added dropwise to a solution of 16.2 g of 2-aminomethyl-3-[2-hydroxy-3-(N-benzyl-tert.-butylamino)-propoxy]-aniline in a mixture of 150 ml of isopropanol and 150 ml of water, at 15°-20°, whilst stirring and cooling with ice. The reaction mixture is stirred at room temperature for a further 2 hours and then evaporated. The residue is dissolved in 100 ml of water, the solution is extracted with 50 ml of ether and the aqueous phase is rendered alkaline with concentrated ammonia and extracted 3 times with, in each case, 200 ml of ethyl acetate. The residue which remains after evaporating the organic phase is dissolved in 50 ml of methanol and boiled with 4.86 g of sodium methylate under reflux for 3 hours. The crystalline precipitate which gradually forms is filtered off after cooling the reaction mixture in an ice bath, whereupon 5-[3-(N-benzyl-tert.-butylamino)-2-hydroxy-propoxy]-3,4-dihydro-1H-quinazolin-2-one with a melting point of 215°-217° is obtained.

Workup

  1. temperaturecooling with ice
  2. stirringThe reaction mixture is stirred at room temperature for a further 2 hours
  3. customevaporated
  4. dissolutionThe residue is dissolved in 100 ml of water
  5. extractionthe solution is extracted with 50 ml of ether
  6. extractionextracted 3 times with, in each case, 200 ml of ethyl acetate
  7. customafter evaporating the organic phase
  8. dissolutionis dissolved in 50 ml of methanol
  9. temperatureunder reflux for 3 hours
  10. filtrationThe crystalline precipitate which gradually forms is filtered off
  11. temperatureafter cooling the reaction mixture in an ice bath

Sources & evidence

ORD record
ord-e0bdccd5b5a348729591775c971a8c35
Source dataset
uspto-grants-1979_02
Patent number
US04140789

Reaction notes

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