Hydrochloric Acid → Triazamate

HRID 1109242Notes

Reaction equation

HRID 1109242 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([S:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][N:18]([CH3:22])[C:19](Cl)=[O:20].C(N(CC)CC)C.Cl>C1COCC1.CN(C)C1C=CN=CC=1.O.C(OCC)C>[CH3:17][N:18]([CH3:22])[C:19]([N:7]1[C:8]([S:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:9][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6]1)=[O:20]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 178473166HCID 178473166, compound

Product 1

HCID 86306TriazamateYield 96.8%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 813 g (3.34 mole) of 3-t-butyl-5-carboethoxymethylthio-1,2,4-1H-triazole in 2 liters of THF was added 395 g (3.67 mole) of dimethyl carbamoyl chloride and 50 g (0.4 mole) of 4-dimethylaminopyridine. To this solution is slowly added 675 g (6.68 mole) of triethylamine, whereon the reaction exotherms to reflux. The reaction is allowed to react for an additional 1.5 hours whereon the temperature slowly returns to room temperature. One liter of ethyl ether, 2 liters of water, 2 kgs of ice are added and the mixture is acidified with concentrated aqueous hydrochloric acid. The aqueous layer is separated and backwashed with 1 liter of ethyl ether before discarding. The combined aqueous layers are washed with 2 liters of brine, dried over magnesium sulfate, and concentrated under vacuum to afford 1016 g of 1-dimethylcarbamoyl-3-t-butyl-5-carboethoxymethylthio-1,2,4-1H-triazole as a tan solid.

Workup

  1. temperatureto reflux
  2. customto react for an additional 1.5 hours whereon the temperature
  3. customslowly returns to room temperature
  4. customThe aqueous layer is separated
  5. washThe combined aqueous layers are washed with 2 liters of brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-37735e1d896c45d88ecbe4eeeaa72d4e
Source dataset
uspto-grants-1994_06
Patent number
US05319092

Reaction notes

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