Sodium Iodide → 5-(2-Morpholin-4-yl-ethyl)-[1,3,4]thiadiazol-2-ylamine

HRID 908184Notes

Reaction equation

HRID 908184 reaction equation
Cl[CH2:2][CH2:3][C:4]1[S:8][C:7]([NH2:9])=[N:6][N:5]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[I-].[Na+].C(N(CC)CC)C>C1(C)C=CC=CC=1>[N:10]1([CH2:2][CH2:3][C:4]2[S:8][C:7]([NH2:9])=[N:6][N:5]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8083MorpholineHCID 8471TriethylamineHCID 150317075-(2-Chloroethyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 31640585-(2-Morpholin-4-yl-ethyl)-[1,3,4]thiadiazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-(2-chloro-ethyl)-[1,3,4]thiadiazol-2-ylamine (54a) (2.5 g, 15.3 mmol), morpholine (2.67 g, 30 mmol) and sodium iodide (0.15 g) is heated with stirring in toluene at 80° C. After adding triethylamine (2.13 ml, 15.3 mmol) heating is continued for an additional 4 hours. The solvent is removed and the residue is partitioned between water (pH 13) and n-butanol. The organic extract is dried (MgSO4) and the solid is removed to afford the titled compound as a yellow solid.

Workup

  1. temperatureis heated
  2. temperatureheating
  3. customThe solvent is removed
  4. customthe residue is partitioned between water (pH 13) and n-butanol
  5. extractionThe organic extract
  6. dry with materialis dried (MgSO4)
  7. customthe solid is removed

Sources & evidence

ORD record
ord-632fbb7956ed4b679965c9036937617a
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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