3-Amino-1,2-propanediol → 3-{[2-(3,4-Dichlorophenyl)quinazolin-4-yl]amino}propane-1,2-diol

HRID 1973355Notes

Reaction equation

HRID 1973355 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[N:3]=1.[OH:20][CH:21]([CH2:24][OH:25])[CH2:22][NH2:23]>CN(C)C=O.O>[Cl:19][C:14]1[CH:13]=[C:12]([C:4]2[N:3]=[C:2]([NH:23][CH2:22][CH:21]([OH:20])[CH2:24][OH:25])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

5

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 214913484-Chloro-2-(3,4-dichlorophenyl)quinazoline

Product 1

HCID 214913463-{[2-(3,4-Dichlorophenyl)quinazolin-4-yl]amino}propane-1,2-diol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 46.5 g. (0.15 mole) of 4-chloro-2-(3,4-dichlorophenyl)quinazoline in 500 ml of dimethylformamide and 29 g (0.31 mole) of 2,3-dihydroxypropylamine was heated on a steam bath with stirring for 4 hrs. Diluted the mixture with water until turbid and cooled in an ice bath. The colorless solid was filtered and recrystallized from methyl alcohol (Darco). The product was collected as colorless needles melting at 155°-160° (with previous softening) in a yield of 49 g. (90%). Further recrystallization from nitromethane gave 39 g. melting at 162°-164°. Anal. Calcd. for C17H15Cl2N3O2 : C, 56.06; H, 4.15; N, 11.54 Found: C, 55.63; H, 4.04; N, 11.49.

Workup

  1. additionA mixture of 46.5 g
  2. temperaturecooled in an ice bath
  3. filtrationThe colorless solid was filtered
  4. customrecrystallized from methyl alcohol (Darco)
  5. customThe product was collected as colorless needles melting at 155°-160° (with previous softening) in a yield of 49 g
  6. customFurther recrystallization from nitromethane
  7. customgave 39 g

Sources & evidence

ORD record
ord-eeeef66c597c44fa99ba7141a2d94757
Source dataset
uspto-grants-1976_12
Patent number
US03997538

Reaction notes

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