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

HRID 2268107Notes

Reaction equation

HRID 2268107 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

Two equivalents of phosgene (1.89 M in toluene; 4.2 ml) are added to a solution of 995 mg of 9H-fluoren-9-yl-methyl 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 (“A”).

Sources & evidence

ORD record
ord-3b3719b6b2cb4825a204e06f2231c490
Source dataset
uspto-grants-2001_12
Patent number
US06326403B1

Reaction notes

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