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Bis(trimethylsilyl)carbodiimide → HCID 178511858, compound

HRID 1503372
Notes
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Reaction equation

HRID 1503372 reaction equation
O=[C:2]1[C:10]2([CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11]2)[CH2:9][C:8]2[C:3]1=[CH:4][C:5]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[C:23]#[N:24])=[CH:6][CH:7]=2.[C:28](=[N:34][Si](C)(C)C)=[N:29][Si](C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:23]([C:22]1[CH:21]=[C:20]([C:5]2[CH:4]=[C:3]3[C:8](=[CH:7][CH:6]=2)[CH2:9][C:10]2([CH2:19][CH2:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH2:11]2)/[C:2]/3=[N:34]/[C:28]#[N:29])[CH:27]=[CH:26][CH:25]=1)#[N:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 665847763-(1-oxo-1,3,3',4'-tetrahydro-1'H-spiro[indene-2,2'-naphthalene]-6-yl)benzonitrile

Product 1

HCID 178511858HCID 178511858, compoundYield 133.9%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344Dichloromethane
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(1-oxo-1,3,3′,4′-tetrahydro-1′H-spiro[indene-2,2′-naphthalene]-6-yl)benzonitrile (35 mg, 0.1 mmol) in DCM (5 mL) was added TiCl4 (76 mg, 0.4 mmol) dropwise, the mixture was stirred at 50° C. at Ar2 under microwave for 5 minutes, N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (74 mg, 0.4 mmol) was added dropwise. The mixture was stirred at 60° C. at Ar2 under microwave for 10 minutes and poured into ice-water (10 mL). The aqueous layer was extracted with CH2Cl2, which was combined with the organic layer. The organic layer was dried and concentrated to give crude (Z)—N-(5-(3-cyanophenyl)-3′,4′-dihydro-1′H-spiro[indene-2,2′-naphthalene]-3(1H)-ylidene)cyanamide (50 mg, 93%).

Workup

  1. stirringThe mixture was stirred at 60° C. at Ar2 under microwave for 10 minutes
  2. extractionThe aqueous layer was extracted with CH2Cl2, which
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d6eab2cc3d694876b880d11926e6b580
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09212153B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes