Pyridine → HCID 54189901, compound

HRID 583205Notes

Reaction equation

[C:1]1([C@H:7]2[CH2:11][N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][CH2:19][CH2:18]4)(=[O:14])=[O:13])[C:9](=[O:24])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[N+:31]([C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1)([O-:33])=[O:32].C(OC(=O)C)C.CCCCCC>ClCCl>[C:1]1([C@H:7]2[CH2:11][N:10]([S:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([C:38](=[O:39])[C:37]3[CH:36]=[CH:35][C:34]([N+:31]([O-:33])=[O:32])=[CH:42][CH:41]=3)[CH2:19][CH2:18]4)(=[O:14])=[O:13])[C:9](=[O:24])[NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 5 °C

Procedure

(S)-(+)-4-phenyl-1-(indoline-5-sulfonyl)-4,5-dihydro-2-imidazolone (0.72 g, 2.09 mmol) prepared in Preparation 8 was dissolved in 20 m of dichloromethane. Then, pyridine (186 μ, 2.23 mmol) and 4-nitrobenzoyl chloride (413 mg, 2.23 mmol) were added thereto at 0° C. under nitrogen atmosphere one after another. The reaction mixture was stirred at 5° C. for 2 hours and further stirred at room temperature for 3 hours. Then, the reaction mixture was diluted with 20 m of dichloromethane, washed with water, dried over anhydrous magnesium sulfate, concentrated and finally purified by silica gel column chromatography (eluent: ethylacetate/hexane=2/1, v/v) to afford 0.97 g (Yield: 93%) of (S)-(+)-4-phenyl-l-[N-(4-nitrobenzoyl)-indoline-5 -sulfonyl]-4,5-dihydro-2-imidazolone.

Workup

customat 0° C.
stirringfurther stirred at room temperature for 3 hours
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customfinally purified by silica gel column chromatography (eluent

Sources & evidence

ORD record: ord-c97be6fc6b9546d49d08e89f4f4c8629
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05929103

Reaction notes

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