Methyl iodide → HCID 69461358, compound

HRID 1297120Notes

Reaction equation

HRID 1297120 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([O:22][CH2:23][CH3:24])=[CH:6][C:7]2[NH:13][C:12](=[O:14])[CH2:11][N:10]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1)[CH3:2].CI.[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:27]([N:13]1[C:7]2[CH:6]=[C:5]([O:22][CH2:23][CH3:24])[C:4]([O:3][CH2:1][CH3:2])=[CH:21][C:8]=2[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:10][CH2:11][C:12]1=[O:14])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 7498Benzyl BromideHCID 9858430HCID 9858430, compound

Product 1

HCID 69461358HCID 69461358, compoundYield 32%

Procedure

By replacing 5-(4-bromophenyl)-7,8-dimethoxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one (XXIIaf) in example IIba by 7,8-diethoxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (XXIIag), and MeI by benzyl bromide, and proceeding in the same manner, the abovenamed product is obtained. Yield: 32%. M: 158–160° C. 1H-NMR (CDCl3, 300 MHz): d 1.33 (t, 3H, CH3), 1.40 (t, 3H, CH3), 3.84–3.95 (m, 3H, OCH2+1H CH2) 4.04 (q, 2H OCH2), 4.87 (m, 1H CH2), 5.15 (AB system, ? d=0.74, JAB=15.4, 2H, —NCH2), 6.58 (s, 1H Ar), 6.81 (s, 1H Ar), 7.07–7.46 (m, 10H Ar).

Workup

  1. customthe abovenamed product is obtained
  2. custom158–160° C

Sources & evidence

ORD record
ord-8c3b2673bcce4e77901383de443c7803
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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