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

HRID 480004Notes

Reaction equation

HRID 480004 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH:5]([C:7]([O:9][CH2:10][CH:11]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[NH2:6]>ClCCl.C([O-])(O)=O.[Na+]>[CH:13]1[C:12]2[CH:11]([CH2:10][O:9][C:7]3[O:8][C:1](=[O:2])[NH:6][N:5]=3)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 1618839-Fluorenylmethyl carbazate

Product 1

HCID 107551765-(9H-fluoren-9-ylmethoxy)-3H-1,3,4-oxadiazol-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2 equivalents of phosgene (1.89M in toluene; 4.2 ml) are added to a solution of 3.91 mmol of 9H-fluoren-9-ylmethyl hydrazinecarboxylate in 40 ml of dichloromethane and 40 ml of saturated aqueous NaHCO3 solution. The mixture is stirred for 15 minutes and then worked up as usual, giving 5-(9H-fluoren-9-ylmethoxy)-3H-[1,3,4]oxadiazol-2-one (“AB”)

Sources & evidence

ORD record
ord-728710c8c000479a9e867cffef8a96bb
Source dataset
uspto-grants-2003_11
Patent number
US06649613B1

Reaction notes

Loading…