Hexamethyldisilazane → HCID 58482538, compound

HRID 1960141Notes

Reaction equation

HRID 1960141 reaction equation
C([O:4][P:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([C:19]2[NH:23][C:22]3[CH:24]=[C:25]([Cl:40])[C:26]([C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[CH:30][CH:29]=4)=[CH:27][C:21]=3[N:20]=2)=[O:18])[CH:12]=1)(=[O:10])[O:6]C(C)C)(C)C.C[Si](N[Si](C)(C)C)(C)C.Br[Si](C)(C)C>C(Cl)Cl>[C:31]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][C:28]([C:26]2[C:25]([Cl:40])=[CH:24][C:22]3[NH:23][C:19]([C:17]([C:13]4[CH:12]=[C:11]([P:5](=[O:4])([OH:10])[OH:6])[CH:16]=[CH:15][CH:14]=4)=[O:18])=[N:20][C:21]=3[CH:27]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 13838HexamethyldisilazaneHCID 76113BromotrimethylsilaneHCID 86761788HCID 86761788, compound

Product 1

HCID 58482538HCID 58482538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 14-3 (56 mg, 0.098 mmol) in 2 mL of CH2Cl2 was added hexamethyldisilizane (0.3 mL), followed by bromo trimethylsilane (0.13 mL, 0.98 mmol). The reaction was allowed to stir for 18 h at ambient temperature. The organic solvent was removed in vacuo, followed by the addition of H2O (2 mL). The crude product was sonicated and yielded a yellow suspension. The product was collected by vacuum filtration and washed three times with CH2Cl2 and two times with MeOH. The product was then dried in vacuo to give the title compound 14-4 as a yellow solid. 1H NMR δ 7.37-7.42 (1H, m), 7.47-7.57 (5H, m), 7.73-7.77 (5H, m), 7.95 (2H, t), 8.60 (2H, t); LC-MS: m/e 489(M+H)+.

Workup

  1. customThe organic solvent was removed in vacuo
  2. additionfollowed by the addition of H2O (2 mL)
  3. customThe crude product was sonicated
  4. customyielded a yellow suspension
  5. filtrationThe product was collected by vacuum filtration
  6. washwashed three times with CH2Cl2 and two times with MeOH
  7. customThe product was then dried in vacuo

Sources & evidence

ORD record
ord-90e8c509eea841a195ad0098baa85171
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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