N-Phenyl diethanolamine → 6-Phenyl-1,3,6-dioxazocan-2-one

HRID 1504568Notes

Reaction equation

HRID 1504568 reaction equation
[C:1]1([N:7]([CH2:11][CH2:12][OH:13])[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[C:1]1([N:7]2[CH2:11][CH2:12][O:13][C:22](=[O:24])[O:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8416N-Phenyl diethanolamineHCID 8471TriethylamineHCID 94429Triphosgene

Product 1

HCID 1183802936-Phenyl-1,3,6-dioxazocan-2-oneYield 55.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure of Example 1 was followed using N-phenyldiethanolamine (15.2 g, 83.9 mmol), triethylamine (24.0 mL, 167.8 mmol), dry THF (600 mL) and triphosgene (8.3 g, 28.8 mmol). The filtrate was concentrated yielding a clear oil containing a mixture of products. The product was purified using a column chromatography EtOAc:Hexanes (3:1) yielding 3.3 g (19%) of a clear oil which turned brown over time.

Workup

  1. concentrationThe filtrate was concentrated
  2. customyielding a clear oil
  3. additioncontaining
  4. additiona mixture of products
  5. customThe product was purified

Sources & evidence

ORD record
ord-948467aa378f4d8caeda1fd24f843fe1
Source dataset
uspto-grants-2015_12
Patent number
US09215876B2

Reaction notes

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