Water → HCID 18965314, compound

HRID 2226738Notes

Reaction equation

[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28]Cl.O>C(OCCCC)CCC.ClCCl>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

Conditions

Temperature: 135 °C

Procedure

Phenothiazine (3.8 g, 19 mmol) was added to a suspension of sodium hydride (0.92 g, 23 mmol, 60% oil dispersion) in dry dibutylether (25 ml) under an atmosphere of nitrogen. The mixture was heated at 135° C. for 1 h and then cooled to approximately 100° C. 2-(2-((tetrahydro-2-pyranyl)oxy)ethoxy)ethylchloride (8 g, 38 mmol) was added in one portion and the mixture was heated overnight at 110° C. The reaction mixture was poured into water (250 ml) and extracted with dichloromethane (3×50 ml) and diethyl ether (50 ml). The combined organic extracts were washed with brine and dried over sodium sulphate. The solvent was evaporated in vacuo leaving an oil, which was submitted to column chromatography using dichloromethane as eluent. Collecting the proper fractions afforded 3.9 g of crude 10-(2-(2-((tetrahydro-2-pyranyl)oxy)ethoxy)ethyl)-10H-phenothiazine. TLC: rf=0.72 (SiO2 ; dichloromethane/methanol=19:1).

Workup

temperaturecooled to approximately 100° C
temperaturethe mixture was heated overnight at 110° C
extractionextracted with dichloromethane (3×50 ml) and diethyl ether (50 ml)
washThe combined organic extracts were washed with brine
dry with materialdried over sodium sulphate
customThe solvent was evaporated in vacuo
customleaving an oil, which
customCollecting the proper fractions

Sources & evidence

ORD record: ord-d6041f89af2f4048ba1c3adb14d74cf5
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05348965

Reaction notes

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