Dimethylformamide → HCID 9842154, compound

HRID 963447Notes

Reaction equation

HRID 963447 reaction equation
[H-].[Na+].[CH2:3]([C:6]1[NH:7][C:8]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:9]=2[N:10]=1)[CH2:4][CH3:5].Br[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1.[CH3:30]N(C=O)C>>[CH2:27]([O:26][C:24](=[O:25])[C:23]1[CH:28]=[CH:29][C:20]([CH2:19][N:10]2[C:9]3[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:8]=3[N:7]=[C:6]2[CH2:3][CH2:4][CH3:5])=[CH:21][CH:22]=1)[CH3:30]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 838516HCID 838516, compound

Product 1

HCID 9842154HCID 9842154, compound

Procedure

To a suspension of sodium hydride, 60% dispersion in oil (1.0 g; 25 mmol) in DMF (30 mL), a solution of 2-propyl-5-nitrobenzoimidazole (4.2 g; 20 mmol) in DMF (30 mL) was added dropwise over 10 minutes. After addition, the reaction mixture was stirred at ambient temperature for 30 minutes, then methyl 4- (bromomethyl)benzoate (4.7 g; 20 mmol) was added. The reaction mixture was heated at 80° C. for 18 hours, then concentrated to a thick oil. The oil was extracted with ethyl acetate and water. The ethyl acetate layer was concentrated to dryness. The residue (1.3 g) was subjected to flash chromatography on silica gel (hexane/EtOAc; 7:3) to obtain 365 mg of yellow solid. Recrystallization from hexane/EtOAc gave the title compound, m.p. 136°-138° C. Anal. Calcd. for C20H21N3O4 : C, 65.38; H, 5.74; N, 11.44.. Found: C, 65.15; H, 5.75; N, 11.26. Mass spectrum (EI; M+) m/z 367. 1H-NMR (DMSO-d6 ; 400 MHz) δ 8.5 (d, 1H), 8.1 (dd, 1H), 7.9 (d, 2H), 7.7 (d, 1H), 7.2 (d, 2H), 5.7 (s, 2H), 4.3-4.3 (q, 2H), 2.8 (t, 2H), 1.7-2.0 (m, 2H), 1.24-1.3 (t, 3H), and 0.90-0.95 ppm (t, 3H).

Workup

  1. additionAfter addition
  2. temperatureThe reaction mixture was heated at 80° C. for 18 hours
  3. concentrationconcentrated to a thick oil
  4. extractionThe oil was extracted with ethyl acetate and water
  5. concentrationThe ethyl acetate layer was concentrated to dryness

Sources & evidence

ORD record
ord-27c6b869903d4822bdf1711bd051860e
Source dataset
uspto-grants-1998_06
Patent number
US05763473

Reaction notes

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