Acetic Anhydride → N-(11-Oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-acetamide

HRID 895976Notes

Reaction equation

HRID 895976 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.C(N(CC)CC)C.[C:25](OC(=O)C)(=[O:27])[CH3:26]>O1CCCC1>[O:11]=[C:10]1[NH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[NH:6][C:5]2[CH:16]=[CH:17][C:2]([NH:1][C:25](=[O:27])[CH3:26])=[CH:3][C:4]1=2

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 107755612-Amino-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one

Product 1

HCID 22349268N-(11-Oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-acetamideYield 50.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one (Example 6, 200 mg, 0.89 mmol) and triethylamine in tetrahydrofuran (10 mL) was cooled to 0° C. (ice-water bath). To this was added acetic anhydride (90.6 mg, 0.89 mmol) dropwise over a period of 10 minutes. The mixture was allowed to warm to room temperature and stirred overnight. The mixture was concentrated at reduced pressure and the residue was chromatographed on silica gel (80% ethyl acetate/20% hexanes then 100% ethyl acetate and finally 2% methanol/ethyl acetate) to give a yellow solid (120 mg, 50.4%). H1 NMR (DMSO d6) δ: 9.82 (s, 1H), 9.80 (s, 1H), 7.82-7.81 (d, 1H, J=4.0), 7.68 (s, 1H), 7.58-7.55 (m, 11H), 6.95-6.86 (m, 5H), 1.97 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated at reduced pressure
  2. customthe residue was chromatographed on silica gel (80% ethyl acetate/20% hexanes

Sources & evidence

ORD record
ord-43548051d4394759ae74eed90c9aa334
Source dataset
uspto-grants-2005_07
Patent number
US06919328B1

Reaction notes

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