Chlorosuccinimide → HCID 136613159, compound

HRID 570917Notes

Reaction equation

HRID 570917 reaction equation
[C:1]([O:5][C:6]([NH:8][N:9]1[CH2:14][C:13](/[CH:15]=[N:16]/[OH:17])=[N:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:10]1=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:26]N1C(=O)CCC1=O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][N:9]1[CH2:14][C:13](/[C:15](/[Cl:26])=[N:16]/[OH:17])=[N:12][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:10]1=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 136613147HCID 136613147, compound

Product 1

HCID 136613159HCID 136613159, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-(tert-butoxycarbonylamino)-6-[(E)-hydroxyiminomethyl]-3-oxo-5H-1,2,4-triazine-2-carboxylate (3.20 g, 8.00 mmol) in DMF (11 mL) at room temperature was slowly added N-chlorosuccinimide (“NCS”)) (1.39 g, 10.4 mmol) and the obtained solution was stirred for 20 h at room temperature. After addition of ice water, the mixture was extracted with diethyl ether and the combined organic layers were washed with brine. Drying (Na2SO4) and evaporation under reduced pressure furnished the desired product as a viscous oil which was used as obtained. 1H NMR (400 MHz, CDCl3) 1.48 (s, 9H), 1.62 (s, 9H), 4.60 (s, 2H), 8.05 (s, 1H).

Workup

  1. customat room temperature
  2. extractionthe mixture was extracted with diethyl ether
  3. washthe combined organic layers were washed with brine
  4. customDrying
  5. custom(Na2SO4) and evaporation under reduced pressure

Sources & evidence

ORD record
ord-d06b268f879c4582b8c707f5de3e5192
Source dataset
uspto-grants-2015_05
Patent number
US09024019B2

Reaction notes

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