Sodium Chloride → HCID 13603334, compound

HRID 2309377Notes

Reaction equation

[H-].[Na+].[CH2:3]([N:5]1[C:13]2[CH:12]=[C:11]3[CH2:14][CH2:15][O:16][C:10]3=[CH:9][C:8]=2[CH2:7][C:6]1=[O:17])[CH3:4].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1.[Cl-].[Na+]>CN(C)C=O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([CH:7]2[C:8]3[CH:9]=[C:10]4[O:16][CH2:15][CH2:14][C:11]4=[CH:12][C:13]=3[N:5]([CH2:3][CH3:4])[C:6]2=[O:17])=[O:27])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a slurry of 18 mg. (0.803 mmole) of sodium hydride in 740 ul. of dimethylformamide cooled to -10° C. was added 150 mg. (0.739 mmole) of 5-ethyl-6-oxo-2,3,6,7-tetrahydro-furo[2,3-f]indole. After the evolution of gas ceased, 125 mg. (0.813 mmole) of 4-chlorophenylisocyanate was added and the reaction mixture allowed to warm to 25° C. and stir for 16 hours. The reaction mixture was poured into a saturated solution of sodium chloride--1N hydrochloric acid and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated to dryness in vacuo. The residue was purified by chromatographing on 20 g. of silica gel using ethyl acetate-hexane (1:2, v:v) as the eluant. The final product was recrystallized from diethyl etherdichloromethane, 15 mg. (6% yield), m.p. 175°-176° C.

Workup

additionwas added 150 mg
extractionextracted with ethyl acetate
dry with materialThe extract was dried over magnesium sulfate
concentrationconcentrated to dryness in vacuo
customThe residue was purified by chromatographing on 20 g
customThe final product was recrystallized from diethyl etherdichloromethane, 15 mg

Sources & evidence

ORD record: ord-7d90ce3b40844e9a8fafbbc8451e61b7
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04695571

Reaction notes

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