Bis(trimethylsilyl)carbodiimide → N-(7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-ylidene)cyanamide

HRID 2096607Notes

Reaction equation

HRID 2096607 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[O:6][CH2:7][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][C:10](=O)[C:4]=2[CH:3]=1.[C:20](=[N:26][Si](C)(C)C)=[N:21][Si](C)(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[O:6][CH2:7][CH:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:9][C:10](=[N:26][C:20]#[N:21])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 584241057-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Product 1

HCID 58424178N-(7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-ylidene)cyanamideYield 94%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-one (158 mg, 0.5 mmol) in DCM (5 mL) was added TiCl4 (1 mL, 1 M in CH2Cl2) dropwise within 15 minutes at room temperature. After stirring for 1 h, N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (0.25 mL, 1.11 mmol) was added dropwise. The mixture was stirred at room temperature overnight and poured into ice-water (25 g). The aqueous layer was extracted with CH2Cl2, which was combined with the organic layer. The organic layer was dried and concentrated to give crude N-(7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-ylidene)cyanamide (160 mg, 94%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionThe aqueous layer was extracted with CH2Cl2, which
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a3732c325b77438e9ef8681a669d9b5c
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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