4-Nitrophenyl chloroformate → HCID 59170490, compound

HRID 1445961Notes

Reaction equation

HRID 1445961 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:13]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([O:1][C:12](=[O:13])[O:14][C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)=[CH:3][CH:4]=1)(=[S:7])[NH2:8]

Participants

5

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 27593444-Hydroxythiobenzamide

Product 1

HCID 59170490HCID 59170490, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of p-hydroxythiobenzamide (1.04 mmol) in CH2Cl2 (10 ml) was added 4-dimethylaminopyridine (DMAP, 1.16 mmol) and 4-nitrophenyl chloroformate (1.15 mmol). The reaction mixture was stirred for 10 hr at room temperature. Thin layer chromatography indicated that the formation of the desired product completed. The solvent was removed and the residue was treated with diethyl ether; product a was recovered by filtration and used without further purification (yield 81%).

Sources & evidence

ORD record
ord-b850b3af804b4bb797daa0b9d84e209d
Source dataset
uspto-grants-2010_02
Patent number
US07666907B2

Reaction notes

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