Potassium Carbonate → HCID 22135226, compound

HRID 1826692Notes

Reaction equation

HRID 1826692 reaction equation
Cl.[CH3:2][O:3][NH2:4].C(=O)([O-])[O-].[K+].[K+].[CH3:11][CH:12]1[CH2:18][C:17]2[CH:19]=[C:20]3[O:25][CH2:24][O:23][C:21]3=[CH:22][C:16]=2[C:15]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[C:28]([CH3:35])[CH:27]=2)=[N:14][N:13]1[C:36](O)=[O:37].[N-]1C=CN=C1>CN(C)C=O>[CH3:11][CH:12]1[CH2:18][C:17]2[CH:19]=[C:20]3[O:25][CH2:24][O:23][C:21]3=[CH:22][C:16]=2[C:15]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[C:28]([CH3:35])[CH:27]=2)=[N:14][N:13]1[C:36](=[O:37])[NH:4][O:3][CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 86760089HCID 86760089, compound

Product 1

HCID 22135226HCID 22135226, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.03 g (25.0 millimoles) of methoxy-amine hydro-chloride and 3.45 g (25.0 millimoles) of potassium carbonate are stirred in 75 ml of anhydrous dimethyl formamide for half an hour whereupon 2.17 g (5.0 millimoles) of (±)-7,8-dihydro-8-methyl-5-(3-methyl-4-nitro-phenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carboxylic acid-imidazolide are added. The reaction mixture is stirred for 16 hours, whereupon the solvent is evaporated at a pressure of 55 Pa. The residue is suspended in 100 ml of water, stirred for half an hour, washed with 50 ml of water and dried. The crude product is recrystallized from 30 ml of acetonitrile and washed with 10 ml of diethyl ether. Thus 1.59 g of the desired compound are obtained, yield 77%, mp.: 192–195° C.

Workup

  1. additionare added
  2. customis evaporated at a pressure of 55 Pa
  3. stirringstirred for half an hour
  4. washwashed with 50 ml of water
  5. customdried
  6. customThe crude product is recrystallized from 30 ml of acetonitrile
  7. washwashed with 10 ml of diethyl ether

Sources & evidence

ORD record
ord-9dbe724e60da4d828c11c17d221b0098
Source dataset
uspto-grants-2006_05
Patent number
US07053082B1

Reaction notes

Loading…