Sodium Hydroxide → 5-[(4-Fluorophenyl)methyl]-1,3,4-thiadiazol-2-amine

HRID 1035685Notes

Reaction equation

HRID 1035685 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][NH:12][C:13](=[S:15])[NH2:14])=O)=[CH:4][CH:3]=1.[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[S:15][C:13]([NH2:14])=[N:12][N:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 214972132-[(4-Fluorophenyl)acetyl]hydrazinecarbothioamide

Product 1

HCID 7410595-[(4-Fluorophenyl)methyl]-1,3,4-thiadiazol-2-amineYield 75.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.38 g of 2-[(4-fluorophenyl)acetyl]hydrazinecarbothioamide (1.67 mmol) is added portionwise with stirring. After stirring for 3 hours between 0 and −10° C., water is added dropwise and the mixture is then returned to basic pH with sodium hydroxide, while maintaining a temperature of between 0 and −10° C. The precipitate is filtered off, washed with water and dried. 0.264 g of 5-(4-fluorobenzyl)-1,3,4-thiadiazol-2-amine is obtained.

Workup

  1. stirringAfter stirring for 3 hours between 0 and −10° C.
  2. temperaturewhile maintaining a temperature of between 0 and −10° C
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-020c23712b404d27a896950a23233838
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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