Methyl iodide → HCID 15057253, compound

HRID 1297142Notes

Reaction equation

CO[C:3]1[CH:4]=[CH:5][C:6]2[NH:12][C:11](=[O:13])[CH2:10][N:9]=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[CH:20]=1.[C:21]1(=O)OCC[O:22]1.I[CH3:28]>>[CH3:21][O:22][C:4]1[CH:3]=[CH:20][C:7]2[C:8]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[N:9][CH2:10][C:11](=[O:13])[N:12]([CH3:28])[C:6]=2[CH:5]=1

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 7303Ethylene carbonate

HCID 99432571,4-BENZODIAZP2-ON,5(PH)7MEO

Product 1

HCID 15057253HCID 15057253, compoundYield 76%

Procedure

By replacing 7,8-dimethoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one (XXIIaa) in the example by 7-methoxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (XXIIan), and ethylene carbonate by iodomethane, and proceeding in the same manner, the abovenamed product is obtained. Yield: 76%. M: 114–116° C. 1H-NMR (CDCl3, 300 MHz): d 3.41 (s, 3H, NCH3), 3.90 (s, 3H, OCH3), 4.29 (AB system, ? d=0.99, JAB=10.6, 2H, —CH2), 6.71–6.75 (m, 1H Ar), 6.81–6.82 (m, 1H Ar), 7.22–7.25 (m, 1H Ar), 7.36–7.42 (m, 3H Ar), 7.50–7.62 (m, 2H Ar).

Workup

customthe abovenamed product is obtained
custom114–116° C

Sources & evidence

ORD record: ord-ccf62d807ec848e4aea44af83f27dbe7
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250410B2

Reaction notes

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