Chlorosuccinimide → (αZ)-2-Amino-5-chloro-α-(methoxyimino)-4-thiazoleacetic acid

HRID 2405681Notes

Reaction equation

HRID 2405681 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][CH3:13])/[C:8]([OH:10])=[O:9])[N:6]=1.C1C(=O)N([Cl:21])C(=O)C1>CN(C=O)C>[NH2:1][C:2]1[S:3][C:4]([Cl:21])=[C:5](/[C:7](=[N:11]/[O:12][CH3:13])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acid

Product 1

HCID 12769735(αZ)-2-Amino-5-chloro-α-(methoxyimino)-4-thiazoleacetic acidYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetic acid (15.0 g) in anhydrous DMF (150 mL) was added NCS (11.95 g) and the mixture was stirred at rt for 2-3 hrs. The reaction mixture was concentrated to remove most of the DMF. The resulting oil was added dropwise to DCM (˜600 mL) at 0° C. with stirring. Solid precipitation was collected by filtration, rinsed with DCM and dried under high vacuum to provide a brownish solid (11.8 g, 67%). ESI-MS (EI+, m/z): 236.0. 1H NMR (300 MHz, DMSO-d6) δ 7.60 (br s, 2H), 3.88 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove most of the DMF
  3. additionThe resulting oil was added dropwise to DCM (˜600 mL) at 0° C.
  4. stirringwith stirring
  5. customSolid precipitation
  6. filtrationwas collected by filtration
  7. washrinsed with DCM
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-e7ca478efddc4e2bb7de8af93d0c348e
Source dataset
uspto-grants-2014_08
Patent number
US08809314B1

Reaction notes

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