Hydrochloric Acid → 6'-Bromo-4-(difluoromethyl)spiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

HRID 539383Notes

Reaction equation

HRID 539383 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7]1([CH2:16][CH2:15][CH:14]([CH:17]([F:19])[F:18])[CH2:13][CH2:12]1)[C:6]2=[N:20]S(C(C)(C)C)=O>O1CCOCC1>[Br:2][C:3]1[CH:4]=[C:5]2[C:9]([CH2:8][C:7]3([CH2:16][CH2:15][CH:14]([CH:17]([F:18])[F:19])[CH2:13][CH2:12]3)[C:6]2=[NH:20])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67979575N-(5'-Bromo-4-(difluoromethyl)spiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

Product 1

HCID 679796646'-Bromo-4-(difluoromethyl)spiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (4 M in 1,4-dioxane) (3.26 mL, 13.0 mmol) was added to a suspension of N-(5′-bromo-4-(difluoromethyl)spiro[cyclohexane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Example 128 Step 1, 0.564 g, 1.30 mmol) in 1,4-dioxane (5 mL) and the resulting mixture was stirred under a nitrogen atmosphere at r.t. overnight. The formed precipitate was filtered off and washed with Et2O. The solid was then dissolved in DCM and sat. aq. NaHCO3. The mixture was poured into a phase separator, the organic layer was collected and concentrated to yield the title compound that was used as such in the next step: MS (CI) m/z 328 [M+H]+.

Workup

  1. filtrationThe formed precipitate was filtered off
  2. washwashed with Et2O
  3. dissolutionThe solid was then dissolved in DCM
  4. additionThe mixture was poured into a phase separator
  5. customthe organic layer was collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cb9dd1c46df941ad8653a4bfb21e0007
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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