Hydrochloric Acid → HCID 18930602, compound

HRID 1598904Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[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:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of p-chlorophenylisocyanate (756 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 distilled under reduced pressure to remove solvent. The residue is recrystallized from dichloromethane/diisopropylether to obtain the objective compound 6y (1.48 g, 76%).

Workup

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

Sources & evidence

ORD record: ord-1a85612ca72f4caf86381feef673a78c
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739162

Reaction notes

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