Water → HCID 58638051, compound

HRID 1768465Notes

Reaction equation

HRID 1768465 reaction equation
ClC(Cl)(OC(=O)[O:6][C:7]([Cl:10])(Cl)Cl)Cl.[Si:13]([O:20][CH2:21][C:22]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:26]=[C:25]([C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=2[F:34])[CH2:24][NH:23]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(N(CC)CC)C.O>C1COCC1>[Si:13]([O:20][CH2:21][C:22]1([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:26]=[C:25]([C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=2[F:34])[CH2:24][N:23]1[C:7]([Cl:10])=[O:6])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 58638077HCID 58638077, compound

Product 1

HCID 58638051HCID 58638051, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3.7 g (12.5 mmol) of triphosgene in THF at 0° C. was added dropwise a mixture of 2.5 g (6.2 mmol) of amine 1-8 and 1.74 mL (12.5 mmol) of triethylamine in THF. The reaction was allowed to warm to room temperature overnight with stirring. The mixture was then dumped into water, placed in a separatory funnel, and extracted twice with EtOAc. The combined organic extracts were combined, washed with water, dried over Na2SO4 and concentrated to obtain 6-1 as a brown solid. Data for 6-1: HRMS (ES) calc'd M+H for C24H28ClF2NO2Si: 464.1619. Found: 464.1625.

Workup

  1. customplaced in a separatory funnel
  2. extractionextracted twice with EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54710bd37ba14ef490fe35d235e80e08
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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