Water → HCID 58615937, compound

HRID 2253288Notes

Reaction equation

HRID 2253288 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1.C(N(CC)CC)C.Cl[C:24]([O:26][CH3:27])=[O:25].O>C(Cl)Cl>[CH3:27][O:26][C:24](=[O:25])[N:2]([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si:12]([CH3:13])([CH3:15])[CH3:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 58615942HCID 58615942, compound

Product 1

HCID 58615937HCID 58615937, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

Amine 3 (90.0 g, ˜0.41 mol) was dissolved in methylene chloride (810 ml). Triethylamine (66.6 g, 0.66 mol) was added and the solution was cooled to 5° C. Methyl chloroformate (47.0 g, 0.50 mol) in methylene chloride (100 ml) was then added slowly and the reaction temperature was maintained between 10° C. and 14° C. After addition was complete, the reaction solution was stirred at room temperature for 12 hours. Water (540 ml) was added. Aqueous phase was separated. Organic phase was concentrated to dryness to afford crude compound 4. The crude product was used in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 0.279 (s, 9H), 2.86 (d, br, 3H), 3.774 (s, 3H), 4.484 (s, br, 2H), 7.190 (s, br, 2H), 7.46 (d, 2H, J=8.10 Hz).

Workup

  1. temperaturethe reaction temperature was maintained between 10° C. and 14° C
  2. additionAfter addition
  3. customAqueous phase was separated
  4. concentrationOrganic phase was concentrated to dryness

Sources & evidence

ORD record
ord-e782948c70bf4dd391492c45747422de
Source dataset
uspto-grants-2008_01
Patent number
US07323562B2

Reaction notes

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