Sodium Carbonate → 5-(4-Morpholinylmethyl)-1,3,4-thiadiazol-2-ylamine

HRID 1070599Notes

Reaction equation

HRID 1070599 reaction equation
FC(F)(F)C(O)=O.[N:8]1([CH2:14][C:15](O)=O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[NH2:18][NH:19][C:20]([NH2:22])=[S:21].C(=O)([O-])[O-].[Na+].[Na+]>>[N:8]1([CH2:14][C:15]2[S:21][C:20]([NH2:22])=[N:19][N:18]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 2723789ThiosemicarbazideHCID 69732510(4-Morpholinyl)acetic acid trifluoroacetic acid salt

Product 1

HCID 223971795-(4-Morpholinylmethyl)-1,3,4-thiadiazol-2-ylamineYield 27.3%

Procedure

(4-Morpholinyl)acetic acid trifluoroacetic acid salt (1.0 g) and thiosemicarbazide (0.25 g) are heated in polyphosphoric acid (2.0 g) at 70° C. for 1 h. The mixture is cooled to room temperature and basified with sodium carbonate, which is extracted with CH2Cl2. The organic layer is dried (MgSO4), concentrated, and the residue is chromatographed (CH2Cl2/methanol, 9/1) to give 150 mg of the title compound as a white solid. Physical characteristics: MS (ESI+) m/z 201 (M+H)+.

Workup

  1. extractionis extracted with CH2Cl2
  2. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationconcentrated
  4. customthe residue is chromatographed (CH2Cl2/methanol, 9/1)

Sources & evidence

ORD record
ord-87fa7abbf7ba4f92987386a43f0a8bb0
Source dataset
uspto-grants-2005_06
Patent number
US06903097B2

Reaction notes

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