Hydrochloric Acid → Methyl (4,6-dimethoxy-1,3,5-triazin-2-yl)carbamate

HRID 2164204Notes

Reaction equation

HRID 2164204 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[N:3]=1.[H-].[Na+].[CH3:14][O:15][C:16](=O)[O:17]C.Cl>O1CCCC1>[CH3:14][O:15][C:16](=[O:17])[NH:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 278402-Amino-4,6-dimethoxy-1,3,5-triazine

Product 1

HCID 12803256Methyl (4,6-dimethoxy-1,3,5-triazin-2-yl)carbamateYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Amino-4,6-dimethoxy-1,3,5-triazine (55.3 g) was added portionwise to 50% sodium hydride (38.0 g) in 1000 ml dry tetrahydrofuran at ambient temperature under nitrogen. After the reaction mixture was stirred for 1.25 hours, dimethylcarbonate (50.0 g) was added dropwise. The reaction mixture was stirred 16 hours at ambient temperature under nitrogen and concentrated hydrochloric acid (68 ml) was slowly added followed by 100 ml tetrahydrofuran. Insoluble material was removed via filtration and discarded. The filtrate was dried and the solvent removed under reduced pressure to give a solid which upon crystallization from ethanol afforded 43.9 g of the title compound, m.p. 118°-122° C.

Workup

  1. stirringThe reaction mixture was stirred 16 hours at ambient temperature under nitrogen
  2. customInsoluble material was removed via filtration
  3. customThe filtrate was dried
  4. customthe solvent removed under reduced pressure
  5. customto give a solid which
  6. customupon crystallization from ethanol

Sources & evidence

ORD record
ord-671b731d1db0424c8f407ddc99b837b1
Source dataset
uspto-grants-1985_03
Patent number
US04502882

Reaction notes

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