tert-Butanol → [3-Chloro-4-(3-fluorobenzyloxy)phenyl](6-iodoquinazolin-4-yl)amine hydrochloride

HRID 1725126Notes

Reaction equation

HRID 1725126 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.Cl[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=2)[N:22]=[CH:21][N:20]=1.CC(O)(C)C>ClCCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([I:29])[CH:27]=3)[N:22]=[CH:21][N:20]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 70592633-Chloro-4-(3-fluorobenzyloxy)anilineHCID 111738094-Chloro-6-iodoquinazoline

Product 1

HCID 66623345[3-Chloro-4-(3-fluorobenzyloxy)phenyl](6-iodoquinazolin-4-yl)amine hydrochlorideYield 116.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-Chloro-4-(3-fluoro-benzyloxy)-phenylamine (3.1 g, 12 mmol) and 4-chloro-6-iodo-quinazoline (3.28 g, 11.3 mmol) are dissolved in a 1:1 mixture of DCE:t-BuOH (56 ml). The reaction mixture is refluxed for 19 hours. The product is isolated by suction filtration through sintered glass, washed with excess DCM, and air dried to afford 3.8 g (7.0 mmol, 58%) of the clean desired material.

Workup

  1. temperatureThe reaction mixture is refluxed for 19 hours
  2. customThe product is isolated by suction filtration through sintered glass
  3. washwashed with excess DCM, and air
  4. customdried

Sources & evidence

ORD record
ord-938a591b65684728ad66876d9aefa29d
Source dataset
uspto-grants-2009_02
Patent number
US07488823B2

Reaction notes

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