Isobutylene → HCID 89601751, compound

HRID 570918Notes

Reaction equation

HRID 570918 reaction equation
[CH3:1][C:2]([CH3:4])=[CH2:3].[C:5]([O:9][C:10]([NH:12][N:13]1[CH2:18][C:17](/[C:19](/Cl)=[N:20]/[OH:21])=[N:16][N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:14]1=[O:30])=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:5]([O:9][C:10]([NH:12][N:13]1[CH2:18][C:17]([C:19]2[CH2:1][C:2]([CH3:4])([CH3:3])[O:21][N:20]=2)=[N:16][N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:14]1=[O:30])=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 8255IsobutyleneHCID 8471TriethylamineHCID 136613159HCID 136613159, compound

Product 1

HCID 89601751HCID 89601751, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into an argon-flushed round-bottom flask equipped with rubber septa and argon balloon at −78° C. was condensed gaseous 2-methylprop-1-ene (2.97 g, 53.0 mmol) via cannula. After addition of a solution of tert-butyl 4-(tert-butoxycarbonylamino)-6-[(Z)—C-chloro-N-hydroxy-carbonimidoyl]-3-oxo-5H-1,2,4-triazine-2-carboxylate (2.30 g, 5.30 mmol) in CHCl3 (10.0 mL), triethylamine (0.747 mL, 5.30 mmol) was slowly added via syringe. After completion of the addition, the reaction mixture was allowed to slowly warm up to room temperature overnight. After 20 h stirring, the reaction mixture was quenched with sat. NH4Cl, and the aqueous layer extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The obtained sticky oil was used as obtained. LCMS (Method K) RT 0.96 min. [M−H]− 410.

Workup

  1. customInto an argon-flushed round-bottom flask
  2. customequipped with rubber septa and argon balloon at −78° C.
  3. additionwas slowly added via syringe
  4. additionAfter completion of the addition
  5. customthe reaction mixture was quenched with sat. NH4Cl
  6. extractionthe aqueous layer extracted with EtOAc
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customas obtained
  10. customLCMS (Method K) RT 0.96 min. [M−H]− 410

Sources & evidence

ORD record
ord-f57d54de0954460ebc5bdc388d9f20b8
Source dataset
uspto-grants-2015_05
Patent number
US09024019B2

Reaction notes

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