Water → HCID 54522201, compound

HRID 862404Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=1[C:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]([CH3:23])[C:15](=[O:24])[CH2:14][N:13]=1.CC(C)([O-])C.[K+].[N:31](OCCC(C)C)=[O:32].O>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(O)(=O)C>[CH3:11][O:10][C:5]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[C:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]([CH3:23])[C:15](=[O:24])[C:14](=[N:31][OH:32])[N:13]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a suspension of 9 g of 1,3-dihydro-5-(2,6-dimethoxy-4-methylphenyl)-1-methyl-1,4-benzodiazepin-2-one in 300 ml of toluene are added portionwise, with cooling to -20° C., 7.8 g of potassium tert-butoxide, then the temperature is allowed to rise slowly to 0° C. over 35 minutes, the mixture is cooled to -20° C. and 3.9 g of isoamyl nitrite in 50 ml of toluene are added dropwise. The reaction mixture is then stirred at 0° C. for 90 minutes, followed successively by pouring of the reaction mixture into water, adjustment of the pH to 4 with acetic acid, extraction with ethyl acetate, washing of the organic phase with water, drying over sodium sulphate and evaporation to dryness. The residue is crystallized from isopropyl ether, filtered and dried to give beige crystals melting at 150° C.; Yield=76%.

Workup

additionare added portionwise
temperaturethe mixture is cooled to -20° C.
washwashing of the organic phase with water
dry with materialdrying over sodium sulphate and evaporation to dryness
customThe residue is crystallized from isopropyl ether
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-e38e61af37a54429b37d5610f7ad753c
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719143

Reaction notes

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