Chloroform → HCID 69890624, compound

HRID 1936814Notes

Reaction equation

HRID 1936814 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][N:14]=[C:13]3[NH:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:23][CH:22]=2)=[CH:8][CH:9]=1)=[O:4].C(Cl)(Cl)[Cl:36]>CCO.[OH-].[Na+]>[ClH:36].[CH2:28]([O:27][C:24]1[CH:23]=[CH:22][C:21]([NH:20][C:13]2[C:12]3[C:17](=[CH:18][CH:19]=[C:10]([C:7]4[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:9][CH:8]=4)[CH:11]=3)[N:16]=[CH:15][N:14]=2)=[CH:26][CH:25]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 54544852HCID 54544852, compound

Product 1

HCID 69890624HCID 69890624, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-(4-(4-Benzyloxy-phenylamino)-quinazolin-6-yl)-furan-2-carboxylic acid methyl ester (0.150 g, 0.332 mmol) was suspended in a mixture of EtOH (2 ml) and 2N aqueous NaOH (2 ml). The mixture was stirred at room temperature for 15 mins. To facilitate dissolution, CHCl3 (2 ml) was added and stirring was continued for 3 days, by which time tlc showed there to be no remaining starting material. The organic solvents were removed in vacuo and the residue diluted with water and treated with 2N aqueous HCl to give the product as a yellow solid, which was collected by filtration (0.130 g, 0.274 mmol, 83%); m/z (M+1+) 438.

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 3 days, by which time tlc
  4. customThe organic solvents were removed in vacuo
  5. additionthe residue diluted with water
  6. additiontreated with 2N aqueous HCl

Sources & evidence

ORD record
ord-c9bfc1f52ee94c1db6ba493d583a633b
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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