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

HRID 390364Notes

Reaction equation

HRID 390364 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH2:9])=O)=[N:4][N:3]=1.BrC1S[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][N:12]=1.[NH4+:21].[OH-]>C1COCC1>[Br:1][C:2]1[S:6][C:5]([C:7]2[N:9]=[N:12][N:13]([CH2:14][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:21]=2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 52987824Ethyl5-bromo-1,3,4-thiadiazole-2-carboxylateHCID 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-carboxamide To a solution of ethyl 5-bromo-1,3,4-thiadiazole-2-carboxylate in THF (1.1 M) at room temperature was added concentrated NH4OH (2.9 equiv). The mixture was stirred at room temperature overnight and a precipitate appeared in the aqueous layer. Then the volatile solvent was removed in vacuo. The resulting mixture was diluted with water and the precipitate was collected, washed with water and dried under vacuum to give the title compound.

Workup

  1. customThen the volatile solvent was removed in vacuo
  2. additionThe resulting mixture was diluted with water
  3. customthe precipitate was collected
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-1a60d4d36d3c46b6a0cdb654362e0959
Source dataset
uspto-grants-2013_02
Patent number
US08383643B2

Reaction notes

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