3-Chloro-4-(3-fluorobenzyloxy)aniline → HCID 68751757, compound

HRID 1801861Notes

Reaction equation

HRID 1801861 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.Cl[C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=1)[NH2:17]>O1CCCC1>[ClH:1].[F:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[CH2:22][O:21][C:20]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 111738094-Chloro-6-iodoquinazoline

Product 1

HCID 68751757HCID 68751757, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 180 ml of tetrahydrofuran were dissolved 4-chloro-6-iodoquinazoline (6.0 g) and 3-chloro-4-(3-fluorobenzyloxy)aniline (II-1, 5.2 g), followed by heat refluxing for 3 hours. A precipitate was filtered, and washed with tetrahydrofuran to obtain 4-(4-(3-fluorobenzyloxy)phenylamino)-6-iodoquinazoline hydrochloride (III-1, 10.5 g) as a yellow solid.

Workup

  1. temperatureby heat
  2. temperaturerefluxing for 3 hours
  3. filtrationA precipitate was filtered
  4. washwashed with tetrahydrofuran

Sources & evidence

ORD record
ord-98a3838313784d1fbaa27549038f4e7c
Source dataset
uspto-grants-2013_01
Patent number
US08349857B2

Reaction notes

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