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Dimethylformamide → N-[1-(2-Morpholin-4-ylethyl)benzimidazol-2-yl]-3-nitrobenzamide

HRID 719578
Notes
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Reaction equation

HRID 719578 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[C:7]([NH:9][C:10]1[NH:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[N:11]=1)=[O:8])([O-:3])=[O:2].CN(C=O)C.Cl.Cl[CH2:29][CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C([O-])(O)=O.[Na+]>[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[C:7]([NH:9][C:10]1[N:11]([CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1)=[O:8])([O-:3])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 3572750HCID 3572750, compound2×

Product 1

HCID 11983295N-[1-(2-Morpholin-4-ylethyl)benzimidazol-2-yl]-3-nitrobenzamide

Reagents, catalysts & solvents 2

HCID 180
Acetone
Solvent
HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
54 °C

Procedure

To a suspension of 3-nitro-N-(1H-benzoimidazol-2-yl)-benzamide prepared above in Example 1 (150 mg, 0.532 mmol, 1.0 equiv) in 3 mL of 5:1 acetone:DMF was added 109 mg of 4-(2-chloroethyl)morpholine hydrochloride (0.585 mmol, 1.1 equiv) and 221 mg K2CO3 (1.60 mmol, 3.0 equiv). The resulting suspension was heated to 54° C. with stirring for 3 h. The suspension was then diluted with 10 mL sat. NaHCO3, and the acetone was removed under reduced pressure. The resulting suspension was then diluted with 20 mL CH2Cl2, shaken until no solids remained, and passed through a 20 mm (40 mL) 3M Empore octadecyl (C18) cartridge to remove water. The collected organics were then concentrated under reduced pressure. Purification by flash chromatography (SiO2, 2–4% MeOH/CH2Cl2) gave 124 mg of the product as a tan solid (0.314 mmol). 1H NMR (DMSO-d6, 400 MHz) δ 12.85 (s, 1 H), 8.97 (s, 1 H), 8.61 (d, J=7.6 Hz, 1 H), 8.38 (d, J=7.5 Hz, 1 H), 7.79 (t, J=8.0 Hz, 1 H), 7.58 (t, J=7.6 Hz, 2 H), 7.26 (m, 2 H), 4.42 (t, J=5.9 Hz, 2 H), 3.49 (m, 4 H), 2.75 (t, J=5.9 Hz, 2 H), 2.55 (m, 4 H).

Workup

  1. customthe acetone was removed under reduced pressure
  2. additionThe resulting suspension was then diluted with 20 mL CH2Cl2
  3. stirringshaken until no solids
  4. customto remove water
  5. concentrationThe collected organics were then concentrated under reduced pressure
  6. customPurification by flash chromatography (SiO2, 2–4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-59b2031874bb478cab721faf12d49d90
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07132438B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes