Ammonium Chloride → HCID 22450238, compound

HRID 1871518Notes

Reaction equation

HRID 1871518 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1Br.[Li+].CCC[CH2-].[O:20]1[CH2:25][CH2:24][O:23][C:22]([C:26](N2CCCC2)=[O:27])=[N:21]1.[Cl-].[NH4+]>O1CCCC1.O.C(OCC)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:26]([C:22]1[O:23][CH2:24][CH2:25][O:20][N:21]=1)=[O:27]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 61028n-Butyl lithiumHCID 36801692-(2-bromophenoxy)tetrahydro-2H-pyranHCID 22450237HCID 22450237, compound

Product 1

HCID 22450238HCID 22450238, compoundYield 42.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

5 g (0.0193 mol) of 1-(tetrahydropyran-2-yloxy)-2-bromobenzene (Synthesis 1987, page 951) are dissolved in 20 ml of tetrahydrofuran, and the solution is cooled to -40° C. First, 10.8 g (0.0388 mol) of N-butyllithium (23% strength solution in hexane) and then a 50% strength solution of 7.2 g (0.0195 mol) of 1-(5,6-dihydro-1,4,2-dioxazin-3-yl)-1-(pyrrolidin-1-yl)-methanone in tetrahydrofuran are added dropwise at this temperature, and the mixture is stirred for 10 minutes at -40° C. A solution of 4.2 g (0.0785 mol) of ammonium chloride in 25 ml of water is then added dropwise, diethyl ether is added, the organic phase is separated off, and the aqueous phase is extracted repeatedly using diethyl ether. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The residue crystallizes upon trituration with pentane. The crystals are filtered off and washed twice using 5 ml of diisopropyl ether. 2.4 g (35.8% of theory) of 3-[2-(tetrahydropyran-2-yloxy)-benzoyl]-5,6-dihydro-1,4,2-dioxazine (content according to HPLC analysis: 84%) are obtained.

Workup

  1. customthe organic phase is separated off
  2. extractionthe aqueous phase is extracted repeatedly using diethyl ether
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue crystallizes upon trituration with pentane
  6. filtrationThe crystals are filtered off
  7. washwashed twice

Sources & evidence

ORD record
ord-d0f5e11a13c8456a851397287bedc96a
Source dataset
uspto-grants-2000_08
Patent number
US06103717

Reaction notes

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