4-Nitrobenzaldehyde → HCID 54353415, compound

HRID 1856383Notes

Reaction equation

HRID 1856383 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=1.[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)([O-:10])=[O:9].[C:19](OC(=O)C)(=[O:21])[CH3:20]>>[C:19]([NH:1][C:2]1[S:3][C:4]([CH:7]=[CH:15][C:14]2[CH:17]=[CH:18][C:11]([N+:8]([O-:10])=[O:9])=[CH:12][CH:13]=2)=[N:5][N:6]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 7918Acetic AnhydrideHCID 669491,3,4-Thiadiazole, 2-amino-5-methyl-

Product 1

HCID 54353415HCID 54353415, compoundYield 49.4%

Procedure

A mixture of 21.4 g (0.186 m) of 2-amino-5-methyl-1,3,4-thiadiazole and 380 ml of acetic anhydride was refluxed 1 hr., after which 28.0 g (0.186 m) of p-nitrobenzaldehyde was added and the reaction mixture was refluxed for an additional 16 hrs. After cooling, the solid product was collected on a Buchner funnel, washed in acetone, and air-dried to yield 26.6 g (0.092 m, 49.4%) of the acetamide as a light yellow powder. Purification by washing in hot acetone/dimethylformamide (50/50) yielded small yellow crystals, MP. 341.5°-342.5° C. (dec).

Workup

  1. temperaturewas refluxed 1 hr
  2. temperaturethe reaction mixture was refluxed for an additional 16 hrs
  3. temperatureAfter cooling
  4. customthe solid product was collected on a Buchner funnel
  5. washwashed in acetone
  6. customair-dried

Sources & evidence

ORD record
ord-04215febe1f4496ea43ea4fe63a3a053
Source dataset
uspto-grants-1980_08
Patent number
US04219475

Reaction notes

Loading…