Morpholine → 5-Morpholin-4-yl-1,3,4-thiadiazol-2-amine

HRID 1857974Notes

Reaction equation

HRID 1857974 reaction equation
Br[C:2]1[S:6][C:5]([NH2:7])=[N:4][N:3]=1.OP([O-])([O-])=O.[K+].[K+].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>CN(C=O)C.O>[O:18]1[CH2:19][CH2:20][N:15]([C:2]2[S:6][C:5]([NH2:7])=[N:4][N:3]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 24450Potassium Phosphate, DibasicHCID 36508832-Amino-5-bromo-1,3,4-thiadiazole

Product 1

HCID 15000115-Morpholin-4-yl-1,3,4-thiadiazol-2-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-1,3,4-thiadiazol-2-ylamine, K2HPO4 (5.7 g), and 5.3 ml of morpholine in 20 ml of DMF is heated at 80° C. under nitrogen for 18 hours, then diluted with 50 ml of water. The clear solution is placed in a continuous extractor and extracted with a brisk flow of dichloromethane for 18 hours. The solution is dried over MgSO4 and concentrated under reduced pressure, with toluene azeotropes to remove DMF. Recrystallization of the residual solid from 50 ml of acetonitrile and 100 ml of toluene affords 3.92 g of the title compound.

Workup

  1. extractionextracted with a brisk flow of dichloromethane for 18 hours
  2. dry with materialThe solution is dried over MgSO4
  3. concentrationconcentrated under reduced pressure, with toluene azeotropes
  4. customto remove DMF
  5. customRecrystallization of the residual solid from 50 ml of acetonitrile and 100 ml of toluene

Sources & evidence

ORD record
ord-0de9a08117134d22b61eafa90ca54a35
Source dataset
uspto-grants-2000_11
Patent number
US06150385

Reaction notes

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