Hydrochloric Acid → HCID 10405977, compound

HRID 973584Notes

Reaction equation

HRID 973584 reaction equation
[CH3:1][N:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]1[C:12]2[C:7](=[C:8]([O:13]C)[CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[N:4]=1.B(Br)(Br)Br.[OH-].[Na+].Cl>ClCCl>[CH3:1][N:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]1[C:12]2[C:7](=[C:8]([OH:13])[CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 10067754HCID 10067754, compound

Product 1

HCID 10405977HCID 10405977, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(N-Methylphenylamino)-2-(2-methylphenylamino)-8-methoxyquinazoline (prepared as described in co-pending EP-A-88311461.3) (1.81 g, 0.0049 mol) was dissolved in dichloromethane (50 ml) and cooled to 0°-5° under nitrogen. Boron tribromide (6.25 g, 0.025 mol) was added dropwise via a syringe through a rubber septum over a period of 10 minutes Reaction was stirred 3 hours at 0°-5° and then allowed to rise to room temperature overnight. The reaction mixture was poured onto ice and the pH adjusted to ~12 with sodium hydroxide and then back to neutral with dilute HCl. The organic layer was separated, dried and evaporated to dryness. The solid residue was crystallised from methanol/water to give the title compound (0.66 g), m.p. 174°-175°.

Workup

  1. temperaturecooled to 0°-5° under nitrogen
  2. customReaction
  3. waitto rise to room temperature overnight
  4. additionThe reaction mixture was poured onto ice
  5. customThe organic layer was separated
  6. customdried
  7. customevaporated to dryness
  8. customThe solid residue was crystallised from methanol/water

Sources & evidence

ORD record
ord-18359bd346714ffc9dfeb46fa583b680
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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