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

HRID 1976265Notes

Reaction equation

[O:1]=[C:2]1[N:8]([CH3:9])[CH2:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[NH:4][CH:3]1[CH2:14][C:15]([O:17][CH3:18])=[O:16].CO.C1C=CN=CC=1.Cl[I:28]>C(Cl)Cl>[I:28][C:11]1[CH:12]=[CH:13][C:5]2[NH:4][CH:3]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:2](=[O:1])[N:8]([CH3:9])[CH2:7][C:6]=2[CH:10]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Methyl 2,3,4,5-tetrahydro-3-oxo-4-methyl-1H-1,4-benzodiazepine-2-acetate (80 g, 0.32 mole) was added to CH2Cl2 (400 ml) and MeOH (400 ml). The mixture was heated at 40° C. for 0.5 hr then cooled to 25° C. Pyridine iodine monochloride complex was added in portions (82g, 0.51 mole). After the addition, the reaction was stirred for 10 minutes then CH2Cl2 (400 ml) added. The reaction mixture was stirred for 1.0 hr then washed with sodium metabisulphite solution (5 g+400 ml water), followed by water (400 ml). The temperature was maintained at 30° C. during the washing process. CH2Cl2 (450 ml) was replaced with 60/80 petrol (450 ml by ‘put and take’ distillation. A further portion of CH2Cl2 (200 ml) was replaced with 60/80 petrol, the mixture cooled slowly to 10° C., and the product filtered off and washed with 60/80 petrol. The product was dried in vacuo to yield the title compound (108 g, 92%).

Workup

temperaturethen cooled to 25° C
additionAfter the addition
stirringThe reaction mixture was stirred for 1.0 hr
washthen washed with sodium metabisulphite solution (5 g+400 ml water)
temperatureThe temperature was maintained at 30° C. during the washing process
distillationdistillation
temperaturethe mixture cooled slowly to 10° C.
filtrationthe product filtered off
washwashed with 60/80 petrol
customThe product was dried in vacuo

Sources & evidence

ORD record: ord-ba4e8a4ad6a44e639aeb40e13f9dfcfd
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225465B1

Reaction notes

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