HCID 14620461, compound → (2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetic acid

HRID 653853Notes

Reaction equation

HRID 653853 reaction equation
C([NH:20][C:21]1[S:25][N:24]=[C:23](/[C:26](=[N:30]/[O:31][CH2:32][F:33])/[C:27]([OH:29])=[O:28])[N:22]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:20][C:21]1[S:25][N:24]=[C:23](/[C:26](=[N:30]/[O:31][CH2:32][F:33])/[C:27]([OH:29])=[O:28])[N:22]=1

Participants

3

Reactant 1

HCID 14620461HCID 14620461, compound

Product 1

HCID 11031360(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetic acidYield 35.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Added to trifluoroacetic acid (100 ml) was 2-(5-tritylamino-1,2,4-thiadiazol-3-yl)-(Z)-2-fluoromethoxyiminoacetic acid (13 g). The resulting mixture was stirred at room temperature for 24 hours. Trifluoroacetic acid was distilled off under reduced pressure. Water (100 ml) was added to the residue and an insoluble matter was filtered off. The solvent was distilled off from the filtrate under reduced pressure. The residue was crystallized from a 1:3 mixture of acetone and isopropyl ether, thereby obtaining the target product (2.18 g) as white crystals.

Workup

  1. distillationTrifluoroacetic acid was distilled off under reduced pressure
  2. additionWater (100 ml) was added to the residue
  3. filtrationan insoluble matter was filtered off
  4. distillationThe solvent was distilled off from the filtrate under reduced pressure
  5. customThe residue was crystallized from a 1:3 mixture of acetone and isopropyl ether

Sources & evidence

ORD record
ord-4d20ff8091064d8fa7b59835b1b8f05b
Source dataset
uspto-grants-1992_07
Patent number
US05128465

Reaction notes

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