Ammonia → Ethanol, 2-((4-(4-morpholinyl)-6-propyl-1,3,5-triazin-2-yl)amino)-, carbamate (ester)

HRID 1031877Notes

Reaction equation

HRID 1031877 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11]([NH:13][CH2:14][CH2:15][O:16][C:17](OC3C=CC=CC=3)=[O:18])[N:10]=[C:9]([CH2:26][CH2:27][CH3:28])[N:8]=2)[CH2:3][CH2:2]1.[NH3:29]>ClCCl>[NH2:29][C:17]([O:16][CH2:15][CH2:14][NH:13][C:11]1[N:12]=[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[N:8]=[C:9]([CH2:26][CH2:27][CH3:28])[N:10]=1)=[O:18]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22166509HCID 22166509, compound

Product 1

HCID 3080163Ethanol, 2-((4-(4-morpholinyl)-6-propyl-1,3,5-triazin-2-yl)amino)-, carbamate (ester)Yield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

19.4 g (0.05 mole) of 2-morpholino-4-[[2-[(phenoxycarbonyl)oxy]ethyl]amino]-6-propyl-1,3,5-triazine, dissolved in 100 ml of anhydrous dichloromethane are introduced into one liter of liquid ammonia. Stirring is continued for 7 hours at a temperature of between -35° C. and -45° C. The ammonia is then evaporated and the organic phase is washed successively with an aqueous solution of sodium bicarbonate and with water. It is dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue obtained crystallizes in a 50:50 mixture (v/v) of ethyl acetate-hexane. 15.1 g of 2-[[2-[(aminocarbonyl)oxy]ethyl]amino]-4-morpholino-6-propyl-1,3,5-triazine are obtained.

Workup

  1. customThe ammonia is then evaporated
  2. washthe organic phase is washed successively with an aqueous solution of sodium bicarbonate and with water
  3. dry with materialIt is dried over sodium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue obtained
  6. customcrystallizes in a 50:50 mixture (v/v) of ethyl acetate-hexane

Sources & evidence

ORD record
ord-3d8c08db2a8046a0b89321b203047022
Source dataset
uspto-grants-1990_09
Patent number
US04956367

Reaction notes

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