tert-Butyl carbazate → t-Butyl 3-(1-methyl-3-phenylpropen-2-yl)carbazate

HRID 1489768

Reaction equation

[C:1]1(/[CH:7]=[CH:8]/[C:9](=O)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[NH:13][NH2:14]>>[CH3:10][CH:9]=[C:8]([NH:14][NH:13][C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 70091tert-Butyl carbazate

HCID 637759Benzylideneacetone

Product 1

HCID 69852452t-Butyl 3-(1-methyl-3-phenylpropen-2-yl)carbazate

Procedure

This compound was prepared by the method of Ghali et al. (J. Org. Chem., 1981, 46, 5413-5414) in about 65% overall yield, from trans-4-phenyl-3-buten-2-one and t-butyl carbazate, after crystallization of the crude product from hexane; melting point=76°-79° C.; NMR (CDCl3) 1.24 (d, 3H, CH3); 1.45 (s, 9H, t-butyl CH3); 3.78 (m, 2H, propenyl CH-1, carbazate NH-3); 5.8 -6.29 (m, 2H, carbazate NH-2, propenyl CH-2); 6.53 (d, 1 H, propenyl CH-3); 7.3 (m, 5H, aromatic).

Workup

customafter crystallization of the crude product from hexane

Sources & evidence

ORD record: ord-af58cbcc62bf42cba06e00b5a27eac5f
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05679688

Linked notes

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