N,N'-Dimethylethylenediamine → 4-(3-(Benzylthio)-2-ethylphenyl)morpholin-3-one

HRID 76800

Reaction equation

[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[C:10]=1[CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][C:19]1=[O:24].CNCCNC.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[CH2:1]([S:8][C:9]1[C:10]([CH2:16][CH3:17])=[C:11]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][C:19]2=[O:24])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Intermediate 4 (1.075 g, 3.5 mmol), morpholin-3-one (389 mg, 3.85 mmol), CuI (67 mg, 0.35 mmol), N,N′-dimethylethylene diamine (75 μl, 0.7 mmol) and K2CO3 (1.064 g, 7.7 mmol) were suspended in toluene (30 ml) under argon and heated to 110° C. for 20 h. After cooling to RT the reaction mixture was quenched by addition of 100 ml sat. aq. NH4Cl, 150 ml concentrated NH3 in water and 100 ml water and extracted three times with ethyl acetate. The organic layers were combined and washed with water and sat. aq. NaCl-solution, dried with MgSO4, filtered and evaporated to dryness. The resulting oil crystallizes upon standing and was triturated with n-heptane-MTBE (19:1).

Workup

temperatureAfter cooling to RT the reaction mixture
customwas quenched by addition of 100 ml sat. aq. NH4Cl, 150 ml concentrated NH3 in water and 100 ml water
extractionextracted three times with ethyl acetate
washwashed with water and sat. aq. NaCl-solution
dry with materialdried with MgSO4
filtrationfiltered
customevaporated to dryness
customThe resulting oil crystallizes
customwas triturated with n-heptane-MTBE (19:1)

Sources & evidence

ORD record: ord-7ec6910c258a42a1b1e945b9df3675f2
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835653B2

Linked notes

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