Phosgene → 5-(9H-fluoren-9-ylmethoxy)-3H-1,3,4-oxadiazol-2-one

HRID 1828769Notes

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][NH2:19])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:20]([O-])(O)=[O:21].[Na+].C(Cl)(Cl)=O>C(Cl)Cl.O>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]3[O:17][C:20](=[O:21])[NH:19][N:18]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of N-[(9H-fluoren-9-ylmethoxy)carbonyl]hydrazine (141) (1.49 g, 5.78 mmol), CH2Cl2 (60 ml) and saturated NaHCO3 solution (60 ml) was stirred vigorously at 0° C. for 5 minutes, and the solution was then left for 5 minutes without stirring. Phosgene (1.89 M in toluene, 7.95 ml, 15.0 mmol) was then carefully added to the lower, organic phase using a syringe, and stirring of the reaction mixture was begun again immediately after the addition. After 10 minutes, water (20 ml) and CH2Cl2 (20 ml) were added to the reaction mixture. The phases were then separated rapidly, the aqueous phase was extracted with CH2Cl2 (50 ml), and the combined organic phases were dried over Na2SO4. Removal of the solvent under reduced pressure and drying gave a colourless solid (1.35 g, 4.82 mmol, 83%).

Workup

waitthe solution was then left for 5 minutes
stirringwithout stirring
stirringstirring of the reaction mixture
additionafter the addition
waitAfter 10 minutes
customThe phases were then separated rapidly
extractionthe aqueous phase was extracted with CH2Cl2 (50 ml)
dry with materialthe combined organic phases were dried over Na2SO4
customRemoval of the solvent under reduced pressure
customdrying

Sources & evidence

ORD record: ord-726240ce1d7c4e2f8de4cc0882c90c2a
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060707B2

Reaction notes

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