Dimethylformamide → (2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetyl chloride

HRID 22478Notes

Reaction equation

HRID 22478 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][CH2:13][F:14])/[C:8](O)=[O:9])[N:3]=1.C(Cl)(=O)C([Cl:18])=O.CN(C)C=O>O1CCCC1>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][CH2:13][F:14])/[C:8]([Cl:18])=[O:9])[N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 11031360(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetic acid

Product 1

HCID 11020979(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 30.0 ml of tetrahydrofuran (THF), 11.0 g of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-fluoromethoxyiminoacetic acid were stirred at -20° C., followed by the dropwise addition of a chlorinating reagent, which had been prepared beforehand by gradually adding 6.97 g of oxalyl chloride at 5° C. to a mixture of 80 ml of THF and 4.0 g of N,N-dimethylformamide (DMF) and then reacting them for 30 minutes. After they were reacted for 5 minutes, the reaction mixture was poured into 400 ml of ice water to precipitate crystals. The crystals were collected by filtration, washed with 100 ml of ice water, and then stirred for 30 minutes in 100 ml of n-hexane. After filtration, the resulting crystals were dried under reduced pressure, whereby the title compound was obtained. Yield: 6.70 g (56.3%). Purity: 91.5%.

Workup

  1. additionfollowed by the dropwise addition of a chlorinating reagent, which
  2. customhad been prepared beforehand
  3. customfor 30 minutes
  4. customAfter they were reacted for 5 minutes
  5. customto precipitate crystals
  6. filtrationThe crystals were collected by filtration
  7. washwashed with 100 ml of ice water
  8. filtrationAfter filtration
  9. dry with materialthe resulting crystals were dried under reduced pressure, whereby the title compound
  10. customwas obtained

Sources & evidence

ORD record
ord-19ac882fec884d77b38654727510b7d9
Source dataset
uspto-grants-1995_06
Patent number
US05428173

Reaction notes

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