Hydrochloric Acid → HCID 18930603, compound

HRID 1598905Notes

Reaction equation

[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[O:9])=[CH:3][CH:2]=1.Br.[NH2:12][CH2:13][C:14]([NH:16][C:17]1[CH:30]=[CH:29][CH:28]=[CH:27][C:18]=1[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20])=[O:15].C(N(CC)CC)C.Cl>O1CCCC1.O>[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:9])[NH:12][CH2:13][C:14]([NH:16][C:17]2[CH:30]=[CH:29][CH:28]=[CH:27][C:18]=2[C:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:20])=[O:15])=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of p-tolylisocyanate (655 mg, 4.92 mmol) in tetrahydrofuran (8 ml) is added to a solution of the salt 3a (1.341 g, 4 mmol) prepared in Preparation 3 in tetrahydrofuran (50 ml). Triethylamine (558 μl, 4 mmol) is added at 0° C., and the mixture is stirred at 0° C. for 30 minutes, and then at room temperature overnight. Water and then 10% hydrochloric acid are added, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried (sodium sulfate), and then the solvent is distilled off under reduced pressure. The residue is recrystallized from dichloromethane/diisopropylether to obtain the objective compound 6z (1.31 1 g, 85%).

Workup

customat room temperature
customovernight
extractionthe mixture is extracted with ethyl acetate
washThe extract is washed with water
dry with materialdried (sodium sulfate)
distillationthe solvent is distilled off under reduced pressure
customThe residue is recrystallized from dichloromethane/diisopropylether

Sources & evidence

ORD record: ord-70987d10a8974d87a5e3f49b1418f6a1
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739162

Reaction notes

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