Methyl iodide → HCID 9880314, compound

HRID 1297136Notes

Reaction equation

HRID 1297136 reaction equation
[CH3:1]OC1C(OC)=CC2NC(=O)CN=C(C3C=CC=CC=3)C=2C=1.[CH2:23]([O:25][C:26]1[C:43]([O:44][CH3:45])=[CH:42][C:29]2[C:30]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[N:31][CH2:32][C:33](=[O:35])[NH:34][C:28]=2[CH:27]=1)[CH3:24].C1(=O)OCCO1.IC>>[CH2:23]([O:25][C:26]1[C:43]([O:44][CH3:45])=[CH:42][C:29]2[C:30]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[N:31][CH2:32][C:33](=[O:35])[N:34]([CH3:1])[C:28]=2[CH:27]=1)[CH3:24]

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 7303Ethylene carbonateHCID 9857854HCID 9857854, compoundHCID 9965973HCID 9965973, compound

Product 1

HCID 9880314HCID 9880314, compoundYield 69%

Procedure

By replacing in the example 7,8-dimethoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one (XXIIaa) by 8-ethoxy-7-methoxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (XXIIam), and ethylene carbonate by iodomethane, and proceeding in the same manner, the abovenamed product is obtained. Yield: 69%. M: 138–140° C. 1H-NMR (CDCl3, 200 MHz): d 1.54 (t, 3H, CH3), 3.38 (s, 3H, NCH3), 3.74 (s, 3H, OCH3), 4.18 (q, 2H, —OCH2), 4.29 (AB system, ? d=0.98, JAB=10.5, 2H, —CH2), 6.70 (s, 1H Ar), 6.77 (s, 1H Ar), 7.39–7.43 (m, 3H Ar), 7.63–7.68 (m, 3H Ar).

Workup

  1. customthe abovenamed product is obtained
  2. custom138–140° C

Sources & evidence

ORD record
ord-49907680a59d474781e5f81d14489c57
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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