Chloroform → HCID 69890624, compound

HRID 2306742Notes

Reaction equation

HRID 2306742 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-6087a0a7aead4502b31c3be22f8a7c3a
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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