Ammonium Hydroxide → 5-Bromo-1,3,4-thiadiazole-2-carboxamide

HRID 561190Notes

Reaction equation

HRID 561190 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([O:9]CC)=O)=[N:4][N:3]=1.[NH4+:12].[OH-]>C1COCC1>[Br:1][C:2]1[S:6][C:5]([C:7]([NH2:12])=[O:9])=[N:4][N:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 52987824Ethyl5-bromo-1,3,4-thiadiazole-2-carboxylate

Product 1

HCID 533886795-Bromo-1,3,4-thiadiazole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-bromo-1,3,4-thiadiazole-2-carboxylate (13.5 g, 56.9 mmol) in THF (50 mL) at room temperature was added NH4OH (28 wt. %, 39.6 mL, 164 mmol). The mixture was stirred at room temperature overnight and a precipitate appeared in the aqueous layer. Volatile materials were removed in vacuo. The mixture was diluted with water and the precipitate was collected, washed with water and dried under vacuum to give the title compound. 1H NMR (400 MHz, acetone-d6): δ7.99 (s, 1H), 7.55 (s, 1H).

Workup

  1. customVolatile materials were removed in vacuo
  2. additionThe mixture was diluted with water
  3. customthe precipitate was collected
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3f6697c223e34916bedf03631935459f
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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