1,2-Dichloroethane → HCID 59631038, compound

HRID 1431750Notes

Reaction equation

HRID 1431750 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=2)[C:10]([OH:12])=O)[CH2:3][CH2:2]1.C(Cl)CCl.[CH3:23][NH2:24].C1COCC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:23][NH:24][C:10](=[O:12])[C:9]1[CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH:8]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 8028TetrahydrofuranHCID 59817793HCID 59817793, compound

Product 1

HCID 59631038HCID 59631038, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Prepared according to Procedure U using 3-morpholino-5-nitrobenzoic acid (0.8 g, 3.17 mmol), EDC (1.22 g, 6.34 mmol), DMAP (0.78 g, 6.34 mmol), 2.0M methanamine in THF (2.4 mL, 4.76 mmol), and DCM (12 mL). Purification by column chromatography (silica; 0-75% EtOAc in hexanes) afforded N-methyl-3-morpholino-5-nitrobenzamide as a yellow amorphous solid. Mass Spectrum (ESI) m/e=266.2 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica; 0-75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ea4897af05bb4b99a6d693463a43428f
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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