Dichloromethane → HCID 15058577, compound

HRID 2073912Notes

Reaction equation

[CH2:1]([N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].CS(O[CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH:24]([O:45][C:46]1[CH:51]=[CH:50][N:49]=[CH:48][N:47]=1)[CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])(=O)=O.[Cl:52]CCl>C(O)C>[Cl-:52].[CH2:1]([N+:7]1[CH:11]=[CH:10][N:9]([CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH:24]([O:45][C:46]2[CH:51]=[CH:50][N:49]=[CH:48][N:47]=2)[CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 80 °C

Procedure

1-Hexylimidazole [304 mg (2 millimoles)] was dissolved in 2-[2-[3-octadecyloxy-2-(pyrimidin-4-yloxy)propoxy]ethoxy]ethyl methanesulfonate [800 mg (1.36 millimole)], and the mixture was heated at 80° C. for 2.5 hours. The mixture was dissolved in a mixture of dichloromethane and ethanol (95:5; 60 ml) and shaken with 30% saline for separation into layers. The lower layer collected was concentrated and purified by silica gel column chromatography [Merck, Art. 7734, 30 g (eluent: chloroform-methanol=9:1-65:25)] to give the above-identified compound [760 mg (82%)].

Workup

customThe lower layer collected
concentrationwas concentrated
custompurified by silica gel column chromatography [Merck, Art. 7734, 30 g (eluent: chloroform-methanol=9:1-65:25)]
customto give the above-identified compound [760 mg (82%)]

Sources & evidence

ORD record: ord-565a0a0ff1304d1c94cb5059b500ff86
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04920134

Reaction notes

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