Hexamethyldisilazane → HCID 45273893, compound

HRID 1960149Notes

Reaction equation

HRID 1960149 reaction equation
C([O:4][P:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]2[NH:22][C:21]3[CH:23]=[C:24]([Cl:37])[C:25]([C:27]4[CH:28]=[C:29]5[C:33](=[CH:34][CH:35]=4)[N:32]([CH3:36])[CH:31]=[CH:30]5)=[CH:26][C:20]=3[N:19]=2)[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>[Cl:37][C:24]1[C:25]([C:27]2[CH:28]=[C:29]3[C:33](=[CH:34][CH:35]=2)[N:32]([CH3:36])[CH:31]=[CH:30]3)=[CH:26][C:20]2[N:19]=[C:18]([O:17][C:13]3[CH:12]=[C:11]([P:5](=[O:4])([OH:10])[OH:6])[CH:16]=[CH:15][CH:14]=3)[NH:22][C:21]=2[CH:23]=1

Participants

5

Reactant 3

HCID 13838HexamethyldisilazaneHCID 76113BromotrimethylsilaneHCID 86761790HCID 86761790, compound

Product 1

HCID 45273893HCID 45273893, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 16-8 (70 mg, 0.13 mmol) in 2 mL of CH2Cl2 was added hexamethyldisilizane (0.3 mL), followed by bromo trimethylsilane (0.17 mL, 1.3 mmol). The reaction was allowed to stir for 18 h at ambient temperature. 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 resulting solid was dried in vacuo to give the title compound 16-9 as a white solid. 1H NMR δ 3.83 (3H, s), 6.46 (1H, d, J=3 Hz), 7.19 (1H, d, J=8.5 Hz), 7.36 (2H, m), 7.47 (1H, d, J=9 Hz), 7.53-7.63 (6H, m); LC-MS: m/e 454(M+H)+.

Workup

  1. customOrganic 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 resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-106b396452d14db79daa3d60246e2055
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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