4-Methylmorpholine → 2-(2-Nitrophenyl)propyl chloroformate

HRID 354210Notes

Reaction equation

HRID 354210 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([CH3:13])[CH2:11][OH:12])([O-:3])=[O:2].CN1CCOCC1.O=C(Cl)[O:23][C:24](Cl)(Cl)[Cl:25]>C1COCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([CH3:13])[CH2:11][O:12][C:24]([Cl:25])=[O:23])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 10426DiphosgeneHCID 113897552-(2-Nitrophenyl)propan-1-ol

Product 1

HCID 114479052-(2-Nitrophenyl)propyl chloroformateYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution consisting of 7.2 g 2-(2-nitrophenyl)propanol (39.7 mmol) and 4.4 ml N-methylmorpholine (39.7 mmol) in 15 ml absolute THF are slowly added to 5 ml diphosgene (41.4 mmol) in 10 ml absolute THF at 0° C. in a nitrogen atmosphere through a needle. Having stirred for 1 hour at 0° C., some of the precipitate is sucked off and the filtrate is withdrawn at the high vacuum. 6.91 g of (1) is obtained in the form of a brown oil (71%).

Workup

  1. customthe filtrate is withdrawn at the high vacuum

Sources & evidence

ORD record
ord-995f6925fda549a19df6a335d826d746
Source dataset
uspto-grants-2004_06
Patent number
US06756492B1

Reaction notes

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