1,8-Diazabicyclo(5.4.0)undec-7-ene → N-ethyl-N'-[7-(phenylsulfanyl)-4,5-dihydro-1,3-benzothiazol-2-yl]urea

HRID 9159Notes

Reaction equation

[C:1]1([S:7][C:8]2(SC3C=CC=CC=3)[C:16]3[S:15][C:14]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:13][C:12]=3[CH2:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[CH2:21]([NH:20][C:18]([NH:17][C:14]1[S:15][C:16]2[C:8]([S:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:9][CH2:10][CH2:11][C:12]=2[N:13]=1)=[O:19])[CH3:22]

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of N-[7,7-di(phenylsulfanyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]-N′-ethylurea (700 mg, 1.59 mmol) in THF (14.0 mL) was added DBU (0.36 mL, 2.38 mmol). The reaction mixture was stirred at about 20° C. for about 30 min. The reaction was concentrated in vacuo. The residual yellow oil was taken up in CH2Cl2, washed with AcOH/H2O 1/10 and dried over MgSO4. The organic solvent was removed in vacuo and the residual oil (1.0 g) was used in the next step without further purification.

Workup

concentrationThe reaction was concentrated in vacuo
washwashed with AcOH/H2O 1/10
dry with materialdried over MgSO4
customThe organic solvent was removed in vacuo
customthe residual oil (1.0 g) was used in the next step without further purification

Sources & evidence

ORD record: ord-f52c1f5594b74389a752e81d2ba57891
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091227B2

Reaction notes

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