Benzyl chloroformate → Benzyl 3-(1,3,4-oxadiazol-2-yl)phenylcarbamate

HRID 1040228Notes

Reaction equation

[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][CH:12]=1)[NH2:9].C(=O)(O)[O-].[Na+].CC(C)=O.O.[CH2:23]([O:30][C:31](Cl)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[CH2:23]([O:30][C:31](=[O:32])[NH:9][C:8]1[CH:10]=[CH:11][CH:12]=[C:6]([C:2]2[O:1][CH:5]=[N:4][N:3]=2)[CH:7]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-(1,3,4-oxadiazol-2-yl)aniline (1 g, 6.2 mmol) and sodium bicarbonate (1.1 g, 13 mmol) in a 2:1 mixture of acetone/water (10 mL) was cooled to 0° C. Benzylchloroformate (0.92 mL, 6.5 mmol) was added dropwise over 5 minutes. The reaction mixture was brought to room temperature and stirred for 30 minutes at which point LCMS indicated completion of the reaction. The reaction mixture was diluted with water and filtered on a glass frit to give (3-[1,3,4]Oxadiazol-2-yl-phenyl)-carbamic acid benzyl ester as a white powder (1.7 g, 93%). M+1=296.4

Workup

customwas brought to room temperature
customcompletion of the reaction
filtrationfiltered on a glass frit

Sources & evidence

ORD record: ord-e6f3a0661f7447c6a9082873da5013a5
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552196B2

Reaction notes

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