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

HRID 2042702Notes

Reaction equation

HRID 2042702 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. The precipitate was filtered and washed with Et2O, dried, then washed with water and dried to give the tert-butyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (10.6 g).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with Et2O
  3. customdried
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7ff8e649d6634a288bca58491eff097b
Source dataset
uspto-grants-2013_11
Patent number
US08586584B2

Reaction notes

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