Isobutyryl chloride → HCID 59623752, compound

HRID 1093955Notes

Reaction equation

HRID 1093955 reaction equation
C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[Pb+3].[F:22][CH:23]([F:38])[CH2:24][N:25]1[C:34]2[C:29](=[N:30][CH:31]=[CH:32][N:33]=2)[C:28](=[O:35])[CH2:27][S:26]1(=[O:37])=[O:36].[C:39](Cl)(=[O:43])[CH:40]([CH3:42])[CH3:41]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1.ClCCl.Cl>[Cl:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[C:27]1[S:26](=[O:36])(=[O:37])[N:25]([CH2:24][CH:23]([F:22])[F:38])[C:34]2[C:29]([C:28]=1[O:35][C:39](=[O:43])[CH:40]([CH3:42])[CH3:41])=[N:30][CH:31]=[CH:32][N:33]=2

Participants

9

Reactant 3

HCID 62325Isobutyryl chlorideHCID 59623757HCID 59623757, compoundHCID 178476527HCID 178476527, compound

Product 1

HCID 59623752HCID 59623752, compound

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-chloro-4-methyl-phenyl lead triacetate (0.153 g), 1-(2,2-difluoro-ethyl)-2,2-dioxo-2,3-dihydro-1H-2-λ-6-thia-1,5,8-triaza-naphthalen-4-one (Example 9.4) (0.070 g) and 4-dimethylaminopyridine (“DMAP”) (0.169 g) in anhydrous chloroform (2 ml) and toluene (1 ml) under a nitrogen atmosphere was heated to reflux for four hours. Isobutyryl chloride (53 μl) was added and the reaction mixture heated to reflux for a further two hours. The reaction mixture was then allowed to cool to ambient temperature and diluted with dichloromethane and aqueous hydrochloric acid (2M). The solids were removed by filtration and the filtrate was separated. The aqueous layer was extracted with further dichloromethane. The combined organic extracts were concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 1:6) to give Compound No. C136 of Table C (0.019 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for four hours
  3. temperaturethe reaction mixture heated
  4. temperatureto reflux for a further two hours
  5. customThe solids were removed by filtration
  6. customthe filtrate was separated
  7. extractionThe aqueous layer was extracted with further dichloromethane
  8. concentrationThe combined organic extracts were concentrated
  9. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane 1:6)
  10. customto give Compound No

Sources & evidence

ORD record
ord-47bc5fc963164db8a1f226c8b5517b39
Source dataset
uspto-grants-2012_03
Patent number
US08133849B2

Reaction notes

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