Bis(trimethylsilyl)carbodiimide → N-(6-bromochroman-4-ylidene)cyanamide

HRID 1408702Notes

Reaction equation

HRID 1408702 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[O:8][CH:7](C1C=CC=CC=1)[CH2:6][C:5]2=O.[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:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[N:26][C:20]#[N:21]

Participants

5

Reactant 2

HCID 70473Bis(trimethylsilyl)carbodiimideHCID 584240016-Bromo-7-fluoro-2-phenylchroman-4-one

Product 1

HCID 58424110N-(6-bromochroman-4-ylidene)cyanamideYield 94%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-7-fluoro-2-phenylchroman-4-one (289.3 mg, 1.28 mmol) in DCM (10 mL) was added TiCl4 (2.6 mL, 1 M in CH2Cl2) dropwise within 15 minutes at room temperature. After stirring for 1 h, N,N′-methanediylidenebis(1,1,1-trimethylsilanamine) (0.63 mL, 2.82 mmol) was added dropwise. The mixture was stirred at room temperature overnight and poured into ice-water (50 g). The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layer was dried and concentrated to give crude N-(6-bromochroman-4-ylidene)cyanamide (300 mg, 94%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. customThe combined organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a158e81b847542e684dc42ec2c51cc09
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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