Triphenylphosphine → (5-Methyl-2-morpholin-4-yl-1,3-thiazol-4-yl)triphenylphosphonium chloride

HRID 2221600Notes

Reaction equation

HRID 2221600 reaction equation
[Cl:1]C[C:3]1[N:4]=[C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[S:6][C:7]=1[CH3:8].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[Cl-:1].[CH3:8][C:7]1[S:6][C:5]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[N:4][C:3]=1[P+:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 230763504-(4-Chloromethyl-5-methyl-1,3-thiazol-2-yl)morpholine

Product 1

HCID 23076597(5-Methyl-2-morpholin-4-yl-1,3-thiazol-4-yl)triphenylphosphonium chlorideYield 93.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(4-chloromethyl-5-methyl-1,3-thiazol-2-yl)morpholine (1.00 g), triphenylphosphine (1.13 g) and acetonitrile (50 mL) was heated under reflux for 15 hrs. After concentration of the reaction mixture, the precipitated crystals were washed with acetonitrile and diethyl ether to give (5-methyl-2-morpholin-4-yl-1,3-thiazol-4-yl)triphenylphosphonium chloride as pale-yellow crystals (1.93 g, yield 91%). Recrystallization from acetonitrile-diethyl ether gave colorless prism crystals. melting point: 242-243° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hrs
  3. washAfter concentration of the reaction mixture, the precipitated crystals were washed with acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-e8f1863659194e2687c5a3bb3df80612
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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