O,O-Dipyridin-2-yl carbonothioate → 4-Ethyl-5-isothiocyanatobenzoxazole

HRID 1872786Notes

Reaction equation

HRID 1872786 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[N:7][C:6]=2[C:10]=1[CH2:11][CH3:12].C1C=C(O[C:20](OC2N=CC=CC=2)=[S:21])N=CC=1>ClCCl>[CH2:11]([C:10]1[C:6]2[N:7]=[CH:8][O:9][C:5]=2[CH:4]=[CH:3][C:2]=1[N:1]=[C:20]=[S:21])[CH3:12]

Participants

4

Reactant 2

HCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 154801424-Ethylbenzo[d]oxazol-5-amine

Product 1

HCID 154801434-Ethyl-5-isothiocyanatobenzoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-amino-4-ethylbenzoxazole (3.98 mmol) in dichloromethane (100 mL) is treated with di-2-pyridyl thionocarbonate (4.39 mmol). The mixture is stirred for two hours. The reaction mixture is concentrated under reduced pressure to yield a brown residue. This material is purified by chromatography (silica gel, 20% ethyl acetate/hexanes) to afford 4-ethyl-5-isothiocyanatobenzoxazole.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto yield a brown residue
  3. customThis material is purified by chromatography (silica gel, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a5e1088d2eaa44478a27dc7650a03a53
Source dataset
uspto-grants-2000_08
Patent number
US06110952

Reaction notes

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