Boron tribromide → HCID 19988710, compound

HRID 973580Notes

Reaction equation

HRID 973580 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[N:19]=[C:18]([N:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=2)[CH3:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.B(Br)(Br)Br>ClCCl>[ClH:1].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[N:19]=[C:18]([N:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[CH3:21])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19988672HCID 19988672, compound

Product 1

HCID 19988710HCID 19988710, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Methylphenylamino)-4-(N-methyl-4-methoxyphenylamino)quinazoline hydrochloride (1.6 g, 0.0043 mol) was stirred in dry dichloromethane (50 ml) at 0°-5° under nitrogen. To this solution was added boron tribromide (2.0 ml, 0.0216 mol) dropwise at 0°-5° over 10 minutes. The mixture was stirred for 3 hours at 0°-5° and then allowed to reach room temperature over 16 hours. After pouring onto ice, basifying and neutralising the aqueous phase was extracted with dichloromethane, the organic extracts which dried and evaporated to dryness. The residue afforded crystals of 2-(2-methylphenylamino)-4-(n-methyl-4-hydroxyphenylamino)quinazoline hydrochloride (0.4 g, 23.7%) from ethanolic hydrogen chloride m.p. 317°-319°.

Workup

  1. waitto reach room temperature over 16 hours
  2. additionAfter pouring onto ice
  3. extractionwas extracted with dichloromethane
  4. customthe organic extracts which dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-6fec7f50d0d246a4a8c3ae80f77ad278
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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