Bis(trimethylsilyl)carbodiimide → HCID 178511857, compound

HRID 1503412Notes

Reaction equation

HRID 1503412 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])[CH:9]=2)[CH2:4][C:3]21[CH2:26][C:25]1[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:19]2.[C:27](=[N:33][Si](C)(C)C)=[N:28][Si](C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:14]([C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[CH2:4][C:3]2([CH2:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19]2)/[C:2]/3=[N:28]/[C:27]#[N:33])[CH:18]=[CH:17][CH:16]=1)#[N:15]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 67043729HCID 67043729, compound

Product 1

HCID 178511857HCID 178511857, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(1-oxo-1,1′,3,3′-tetrahydro-2,2′-spirobi[indene]-6-yl)benzonitrile (34 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)-1′,3′-dihydro-2,2′-spirobi[indene]-3(1H)-ylidene)cyanamide (36 mg, 99%).

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-65c0b86350114c02b5d83f8dcfed4727
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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