Methanol → Methyl 2,3,4,5-tetrahydro-7-iodo-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetate

HRID 1976266Notes

Reaction equation

HRID 1976266 reaction equation
[CH3:1][N:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][CH:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:3]1=[O:18].CO.N1C=CC=CC=1.[I:27]Cl>C(Cl)Cl>[I:27][C:10]1[CH:11]=[CH:12][C:6]2[NH:5][CH:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:3](=[O:18])[N:2]([CH3:1])[CH2:8][C:7]=2[CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 24640Iodine chlorideHCID 11770765Methyl 2,3,4,5-tetrahydro-3-oxo-4-methyl-1H-1,4-benzodiazepine-2-acetate

Product 1

HCID 22000810Methyl 2,3,4,5-tetrahydro-7-iodo-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetateYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

Methyl 2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetate (100 g, 0.4 moles) was added to CH2Cl2 (500 ml) plus MeOH (500 ml) and heated at 40° C. for 0.5 hr. The solution was cooled to 26° C. and pyridine (64 g, 0.8 mole) added. Iodine monochloride (71.3 g, 0.44 mole) dissolved in CH2Cl2 (500 ml) was added dropwise over 30 minutes and the reaction stirred for a further 1.0 hr. The product was filtered off, washed with 60/80 petrol and dried in vacuo to yield the title compound (113 g, 75%).

Workup

  1. temperatureThe solution was cooled to 26° C.
  2. additionwas added dropwise over 30 minutes
  3. filtrationThe product was filtered off
  4. washwashed with 60/80 petrol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bc26def87d9549458e7bae4b418cb87e
Source dataset
uspto-grants-2001_05
Patent number
US06225465B1

Reaction notes

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