N,N-Dimethylaniline → HCID 178498371, compound

HRID 539223Notes

Reaction equation

[N:1]1([C:7]2[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[C:10]3[NH:14][C:13](=O)[NH:12][C:11]=3[CH:16]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:32]>>[Cl:32][C:13]1[NH:14][C:10]2[C:9]([C:17]([O:19][CH3:20])=[O:18])=[CH:8][C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:16][C:11]=2[N:12]=1

Participants

Reactant 3

HCID 949N,N-Dimethylaniline

HCID 24813Phosphorus oxychloride

HCID 66976929methyl 6-(4-morpholinyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate

Product 1

HCID 178498371HCID 178498371, compoundYield 23%

Conditions

Temperature: 103 °C

Procedure

To a solution of combined batches of methyl 6-(4-morpholinyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (6.8 g, 24.5 mmol) in POCl3 (25 mL) was added N,N-Dimethylaniline (8.8 g, 73.5 mmol) and the mixture was heated to 103° C. for 12 h. When TLC analysis showed no starting material remaining, the mixture was cooled to room temperature, purified by chromatography (eluted with petroleum ether/EtOAc=1/1) on silica to afford the desired product as a off-white solid (1.6 g, 23%). 1H NMR (300 MHz, DMSO-d6): δ ppm 3.11 (t, 4H, J=4.5 Hz), 3.77 (t, 4H, J=4.5 Hz), 3.93 (s, 3H), 7.43 (d, 1H, J=1.8 Hz), 7.50 (d, 1H, J=1.8 Hz), 12.97 (s, 1H). LC-MS: m/e=296 [M+1]+.

Workup

temperaturethe mixture was cooled to room temperature
custompurified by chromatography (eluted with petroleum ether/EtOAc=1/1) on silica

Sources & evidence

ORD record: ord-7ce318966a9a49e0bfe3544517759cdd
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865912B2

Reaction notes

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