N-Butyldiethanolamine → 6-Butyl-1,3,6-dioxazocan-2-one

HRID 1504565

Reaction equation

HRID 1504565 reaction equation
[CH2:1]([N:5]([CH2:9][CH2:10][OH:11])[CH2:6][CH2:7][OH:8])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.Cl[C:20](Cl)([O:22]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[CH2:1]([N:5]1[CH2:6][CH2:7][O:8][C:20](=[O:22])[O:11][CH2:10][CH2:9]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 7620N-ButyldiethanolamineHCID 8471TriethylamineHCID 94429Triphosgene

Product 1

HCID 1183802946-Butyl-1,3,6-dioxazocan-2-oneYield 239.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure of Example 1 was followed using N-butyl diethanolamine (13.5 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 yellow/brown oil product (12.9 g, 82%).

Workup

  1. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-24c0c767132642f883f7580d4bab7314
Source dataset
uspto-grants-2015_12
Patent number
US09215876B2

Linked notes

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