Triethylamine → Ethyl [5-(5-bromo-1,3,4-thiadiazol-2-yl)-2H-tetrazol-2-yl]acetate

HRID 390365Notes

Reaction equation

HRID 390365 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]#[N:8])=[N:4][N:3]=1.BrC1SC(C(N)=O)=[N:12][N:11]=1.CC[N:20](CC)CC.[C:25]([O:31][C:32]([C:34](F)(F)F)=O)([C:27](F)(F)F)=[O:26]>C1COCC1>[Br:1][C:2]1[S:6][C:5]([C:7]2[N:20]=[N:11][N:12]([CH2:27][C:25]([O:31][CH2:32][CH3:34])=[O:26])[N:8]=2)=[N:4][N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 533885265-Bromo-1,3,4-thiadiazole-2-carbonitrileHCID 533886795-Bromo-1,3,4-thiadiazole-2-carboxamide

Product 1

HCID 59321687Ethyl [5-(5-bromo-1,3,4-thiadiazol-2-yl)-2H-tetrazol-2-yl]acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-1,3,4-thiadiazole-2-carbonitrile To a solution of 5-bromo-1,3,4-thiadiazole-2-carboxamide and Et3N (2.3 equiv) in THF (0.5 M) at 0° C. was added TFAA (1.1 equiv). The mixture was then warmed to room temperature and stirred for 30 min, then the solvent was evaporated in vacuo. The resulting residue was diluted with water. The resulting precipitate was collected, washed with water, and dried to give the title compound.

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionThe resulting residue was diluted with water
  3. customThe resulting precipitate was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ceded20fa0854a9f830da425584a44db
Source dataset
uspto-grants-2013_02
Patent number
US08383643B2

Reaction notes

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