4-Chloro-N-methylbenzenamine → Hydrochloric Acid

HRID 358035

Reaction equation

HRID 358035 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([NH:18][CH3:19])=[CH:16][CH:15]=1>C(O)C>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:18]([CH3:19])[C:17]3[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=3)=[N:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1.[ClH:1]

Participants

5

Reactant 2

HCID 702724-Chloro-N-methylbenzenamineHCID 2418814,7-Dichloroquinazoline

Product 2

HCID 313Hydrochloric AcidHCID 127745177-Chloro-4-(4'-chloro-N-methylanilino)quinazoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.5 g of 4,7-dichloroquinazoline and 2.2 g of p-chloro-N-methylaniline were added to 10 ml of ethanol and then the mixture was heated. The mixture became a homogeneous solution which solidified soon after. After cooling, the solidified crystals were collected and recrystallized from ethanol to give the desired compound in the form of its hydrochloride (Compound No. 68). The crystals of hydrochloride were crushed and added to a dilute aqueous solution of sodium hydroxide, with stirring, to precipitate the free base. The precipitate was collected by filtration, washed with water and recrystallized from ethanol to give 2.4 g (yield 65%) of the desired Compound No. 67 in the form of colourless plates melting at 129°-131° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. customthe solidified crystals were collected
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-eb6788864d8246b19c761fdf5d1dd535
Source dataset
uspto-grants-1984_08
Patent number
US04464375

Linked notes

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