((Isotridecyloxy)methyl)oxirane → 1-[4-(1,1-Dioxo-thiomorpholin-4-yl)-phenoxy]-3-(isotridecyloxy)-propan-2-ol

HRID 619094Notes

Reaction equation

HRID 619094 reaction equation
[O:1]=[S:2]1(=[O:15])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH2:16]([O:29][CH2:30][CH:31]1[O:33][CH2:32]1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[O:15]=[S:2]1(=[O:1])[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:32][CH:31]([OH:33])[CH2:30][O:29][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6454744((Isotridecyloxy)methyl)oxiraneHCID 218452234-(4-Hydroxyphenyl)thiomorpholine 1,1-Dioxide

Product 1

HCID 218452291-[4-(1,1-Dioxo-thiomorpholin-4-yl)-phenoxy]-3-(isotridecyloxy)-propan-2-olYield 50%

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

4-(1,1-dioxo-thiomorpholin-4-yl)phenol (2.3 g, 10 mmol), isotridecylglycidyl ether (2.6 g, 10 mmol) and ethyltriphenylphosphonium bromide (0.1 g) are reacted and purified as described for compound 102 to afford a light yellow liquid 2.4 g (50%).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-c8f22345cdf24488a4199638de845d99
Source dataset
uspto-grants-1999_09
Patent number
US05958663

Reaction notes

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