Diisopropylethylamine → Tert-butyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate

HRID 2093772Notes

Reaction equation

HRID 2093772 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[N:3]=1.[NH2:15][C:16]1[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:18][CH:17]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[N:3]=[C:2]([NH:15][C:16]2[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[CH:18][CH:17]=2)[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 580396362,4-Dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine

Product 1

HCID 86652471Tert-butyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoateYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4-dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine (10 g, 40.3 mmol) in THF (100 mL) was added tert-butyl 4-aminobenzoate (7.79 g, 40.3 mmol) and Hunig's Base (7.04 mL, 40.3 mmol). The resulting mixture was stirred for 16 h. After removal of most THF, the precipitate was filtered and washed with THF, then washed with water and dried to give the product tert-butyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (10.6 g) as white solid.

Workup

  1. customAfter removal of most THF
  2. filtrationthe precipitate was filtered
  3. washwashed with THF
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-61e9d7aa589341adb9d6bfa584dd2e83
Source dataset
uspto-grants-2013_05
Patent number
US08445490B2

Reaction notes

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