Phosgene → HCID 9868930, compound

HRID 1294476Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([NH2:20])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:21](=[O:24])(O)[O-].[Na+].C(Cl)(Cl)=O.[C:30]([C:34]1[CH:35]=[CH:36][C:37]([CH3:41])=[C:38]([CH:40]=1)[NH2:39])([CH3:33])([CH3:32])[CH3:31]>ClCCl>[C:30]([C:34]1[CH:35]=[CH:36][C:37]([CH3:41])=[C:38]([NH:39][C:21]([NH:20][C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([O:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:11][CH:12]=2)=[O:24])[CH:40]=1)([CH3:33])([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 0 °C

Procedure

4-[2-(Morpholin-4-yl)ethoxy]napth-1-yl-amine (280 mg, 1.0 mmol) was dissolved in dichloromethane (15 mL). An equal volume of sat. aqueous sodium bicarbonate was added, and the biphasic solution was cooled to 0° C. During the addition of phosgene (1.93 M in toluene, 1.0 mL), stirring was stopped. Immediately afterward, stirring was resumed for 15 min with the reaction mixture at 0° C. The layers were separated, the organics were dried over solid magnesium sulfate and concentrated to approximately 5 mL of solution. 5-tert-Butyl-2-methylaniline (150 mg, 0.9 mmol) in dichloromethane (5 mL) was added, and the reaction mixture was stirred for 17 h at ambient temperature. The desired compound was obtained after treatment of the reaction mixture with petroleum ether and filtering to collect the precipitate (180 mg, 42%).

Workup

stirringImmediately afterward, stirring
customThe layers were separated
dry with materialthe organics were dried over solid magnesium sulfate
concentrationconcentrated to approximately 5 mL of solution
stirringthe reaction mixture was stirred for 17 h at ambient temperature

Sources & evidence

ORD record: ord-5acbc34d2ac9443d892295aa26d50098
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241758B2

Reaction notes

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