1,1-Dichloroethane → HCID 59631184, compound

HRID 1431766Notes

Reaction equation

HRID 1431766 reaction equation
[C:1]([NH:4][NH:5][C:6](=[O:22])[C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:8]=1)(=O)[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.ClC(Cl)C>>[CH3:2][C:1]1[O:22][C:6]([C:7]2[CH:8]=[C:9]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=2)=[N:5][N:4]=1

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 67509241Benzoic acid, 3-(4-morpholinyl)-5-nitro-, 2-acetylhydrazide

Product 1

HCID 59631184HCID 59631184, compound

Conditions

Temperature
120 °C

Procedure

A 10 mL microwave vessel equipt with a stirbar was charged with N′-acetyl-3-morpholino-5-nitrobenzohydrazide (0.250 g, 0.811 mmol), Burgess reagent (0.97 g, 4.05 mmol), and dichloroethane (4 mL). The red solution was heated in a microwave at 120° C. for 20 minutes, then concd. The resulting residue was partitioned between EtOAc and water, and the organic layer washed with 1 N HCl, 1 N sodium hydroxide, and brine, then dried over magnesium sulfate and concd. This afforded a crude material that was purified by column chromatography (silica; 0-75% EtOAc in hexanes), providing 4-(3-(5-methyl-1,3,4-oxadiazol-2-yl)-5-nitrophenyl)morpholine as a yellow amorphous solid. Mass Spectrum (ESI) m/e=291.1 (M+1).

Workup

  1. customThe resulting residue was partitioned between EtOAc and water
  2. washthe organic layer washed with 1 N HCl, 1 N sodium hydroxide, and brine
  3. dry with materialdried over magnesium sulfate and concd
  4. customThis afforded a crude material that
  5. customwas purified by column chromatography (silica; 0-75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-82d16c3de34d4687ade8bb761974faa2
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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