Hydrochloric Acid → HCID 88233008, compound
Reaction equation
Cl.[NH2:2][OH:3].N1C=CC=CC=1.C[Si](Cl)(C)C.[F:15][C:16]1[CH:41]=[CH:40][C:19]([O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27][CH2:28][C:29]3([C:37](Cl)=[O:38])[CH2:35][CH:34]4[O:36][CH:31]([CH2:32][CH2:33]4)[CH2:30]3)=[CH:23][CH:22]=2)=[CH:18][CH:17]=1.Cl>ClCCl>[OH:3][NH:2][C:37]([C:29]1([CH2:28][S:27][C:24]2[CH:25]=[CH:26][C:21]([O:20][C:19]3[CH:40]=[CH:41][C:16]([F:15])=[CH:17][CH:18]=3)=[CH:22][CH:23]=2)[CH2:35][CH:34]2[O:36][CH:31]([CH2:32][CH2:33]2)[CH2:30]1)=[O:38]Participants
Procedure
A solution of (19.7 mmol, 1.3 equivalents) of hydroxylamine hydrochloride in 9.2 mL (114 mmol, 7.5 equivalents) of dry pyridine at 0° C. is treated with 5.8 mL (45 mmol, 3.0 equivalents) of trimethylsilyl chloride, causing white solids to precipitate. The mixture is allowed to warm to ambient temperature overnight. This mixture is then cooled to 0° C. and treated with a solution of (15.1 mmol) of the product from Step F in 73 mL of dichloromethane causing an exotherm to about 8° C. This mixture is stirred at 0° C. for 30 minutes and at ambient temperature for about one hour. The reaction is then treated with 50 mL of 2N aqueous hydrochloric acid and is stirred at ambient temperature for one hour. The aqueous phase is extracted with dichloromethane and the combined organic phases are washed with 2N aqueous hydrochloric acid (2×50 mL) and water (50 mL). The organic phase is then concentrated to yield the title compound.
Workup
- customto precipitate
- temperatureThis mixture is then cooled to 0° C.
- stirringis stirred at ambient temperature for one hour
- extractionThe aqueous phase is extracted with dichloromethane
- washthe combined organic phases are washed with 2N aqueous hydrochloric acid (2×50 mL) and water (50 mL)
- concentrationThe organic phase is then concentrated
Sources & evidence
- ORD record
- ord-442947e767974e2b8bf9f8db1d4a56a5
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288246B1
Reaction notes
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