Methylamine → HCID 23371653, compound

HRID 1899818Notes

Reaction equation

HRID 1899818 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[N:3]=1.[CH3:18][NH2:19]>C(Cl)Cl>[Cl:8][C:6]1[N:5]=[C:4]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[N:3]=[C:2]([NH:19][CH3:18])[N:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 23371667HCID 23371667, compound

Product 1

HCID 23371653HCID 23371653, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,4-dichloro-6-indolin-1-yl-1,3,5-triazine (30 g, 112 mM) and methylene chloride (300 ml) at 0° C. was added a 33% solution of methylamine (30 ml) in IMS. The mixture was allowed to attain ambient temperature. After two days the mixture was washed with water. The methylene chloride layer was separated, dried (MgSO4), and the solvent evaporated. The resultant solid was recrystallised from toluene: ethanol (70:30). There was thus obtained 2-chloro-4-indolin-1-yl-6-methylamino-1,3,5-triazine (24 g, 82% yield). m.p 239°-240° C.; NMR: DMSOd6 : 2.75-2.95 (3H, complex, rotamers, NHMe), 3.05-3.2 (2H,t,CH2 --CH2N--), 4.0-4.2(2H,q,CH2CH2N) (rotamers), 6.9-7.3(3H, complex, aromatic), 7.9-8.1 (1H, broad, aromatic), 8.1-8.4(1H, broad, NH).

Workup

  1. customto attain ambient temperature
  2. washAfter two days the mixture was washed with water
  3. customThe methylene chloride layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated
  6. customThe resultant solid was recrystallised from toluene: ethanol (70:30)

Sources & evidence

ORD record
ord-aec1d971e4044ceea7f9e33b2fd7eb82
Source dataset
uspto-grants-1996_11
Patent number
US05574037

Reaction notes

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