Ethyl Acetate → 4-chloro-N-(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621422Notes

Reaction equation

HRID 1621422 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][CH:13]=1.C(N(C(C)C)C(C)C)C.CCOC(C)=O>CN(C=O)C>[Cl:8][C:6]1[N:5]=[C:4]([CH3:9])[N:3]=[C:2]([NH:19][CH2:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[N:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 160832,4-Dichloro-6-methyl-1,3,5-triazineHCID 754524-MethoxybenzylamineHCID 81531Diisopropylethylamine

Product 1

HCID 595483604-chloro-N-(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amineYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,4-dichloro-6-methyl-1,3,5-triazine (190 g, 1159 mmol) in DMF (1500 mL) was added (4-methoxyphenyl)methanamine (159 g, 1159 mmol) slowly in 15 min while the temperature was controlled below 20° C. This was followed by the addition of N-ethyl-N-isopropylpropan-2-amine (222 mL, 1274 mmol) slowly over 15 min. After the completion of the reaction, EtOAc (2000 mL) was added and the mixture was washed with dilute brine (200 mL saturated NaCl plus 500 mL water), water (500 mL), saturated NH4Cl (250 mL), and finally water (250 mL). The organic layer was concentrated to afford 4-chloro-N-(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine as a solid (290.5 g, 1097 mmol, 95% yield). m/z 265.2 (M+H).

Workup

  1. customwas controlled below 20° C
  2. additionwas added
  3. washthe mixture was washed with dilute brine (200 mL saturated NaCl plus 500 mL water), water (500 mL), saturated NH4Cl (250 mL), and finally water (250 mL)
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-2dfca0d2ed3e47978f1ca3dd7affaa22
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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