Hydrochloric Acid → 6'-Bromospiro[cyclobutane-1,2'-inden]-1'(3'H)-imine

HRID 1770975

Reaction equation

HRID 1770975 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([CH2:14][CH2:13][CH2:12]1)[C:6]2=[N:15]S(C(C)(C)C)=O.CCOCC>O1CCOCC1>[Br:2][C:3]1[CH:4]=[C:5]2[C:9]([CH2:8][C:7]3([CH2:14][CH2:13][CH2:12]3)[C:6]2=[NH:15])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67979440N-(5'-Bromospiro[cyclobutane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

Product 1

HCID 679793936'-Bromospiro[cyclobutane-1,2'-inden]-1'(3'H)-imine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrochloric acid (4M in 1,4-dioxane, 14.89 mL, 59.55 mmol) was added to a solution of N-(5′-bromospiro[cyclobutane-1,2′-indene]-3′(1′H)-ylidene)-2-methylpropane-2-sulfinamide (Example 54 Step 1, 2.11 g, 5.96 mmol) in anhydrous 1,4-dioxane (60 mL), and the resulting mixture was stirred under an argon atmosphere for 3 h. Et2O (4 mL) was added and the precipitate was filtered off and washed with Et2O, then partitioned between DCM (100 mL), and sat. aq. NaHCO3 (100 mL). The phases were separated and the organic layer concentrated to afford the title compound that was used as such without further purification.

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with Et2O
  3. custompartitioned between DCM (100 mL), and sat. aq. NaHCO3 (100 mL)
  4. customThe phases were separated
  5. concentrationthe organic layer concentrated

Sources & evidence

ORD record
ord-f02e33a4102f4dd9b8542edceb107aa3
Source dataset
uspto-grants-2016_02
Patent number
US09248129B2

Linked notes

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