Triethylamine → HCID 178449016, compound

HRID 1441689Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:11][CH2:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.Cl.[NH2:26][OH:27].C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1.CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:26][OH:27])=[NH:18])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 65 °C

Procedure

290 mg 4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-benzonitrile were dissolved in a mixture of 10 ml tetrahydrofuran and 20 ml methanol. 930 mg hydroxylamine hydrochloride were added followed by the addition of 2.24 ml triethylamine. The reaction mixture was stirred at 65° C. for two hours. The cooled reaction mixture was diluted by the addition of 100 ml ethyl acetate, then washed three times with 40 ml water. The organic layer was dried over MgSO4, then the solvent was removed in vacuo to obtain 280 mg 4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-N-hydroxy-benzamidine as a pale yellow oil.

Workup

customThe cooled reaction mixture
washwashed three times with 40 ml water
dry with materialThe organic layer was dried over MgSO4
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-bef0f04c489748a8807e6bf86835fa51
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655679B2

Reaction notes

Loading…