Sulfuric Acid → HCID 20562355, compound

HRID 848144Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([NH:19][C:20]([N:22]3[CH2:24][CH2:23]3)=[O:21])[CH:17]=[CH:18][C:13]=2[N:12]([CH3:25])[C:11](=[O:26])[CH2:10][N:9]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[C:37]([OH:41])([CH3:40])([CH3:39])[CH3:38]>>[C:37]([O:41][CH2:24][CH2:23][NH:22][C:20]([NH:19][C:16]1[CH:17]=[CH:18][C:13]2[N:12]([CH3:25])[C:11](=[O:26])[CH2:10][N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[C:14]=2[CH:15]=1)=[O:21])([CH3:40])([CH3:39])[CH3:38]

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 6386tert-Butanol

HCID 516892Sodium Bicarbonate

HCID 30582671-Aziridinecarboxamide, N-(5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-

Product 1

HCID 20562355HCID 20562355, compound

Procedure

2 g (0.0057 M) of N-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-1-aziridinecarboxamide in 50 ml of tert.butanol are treated with 3 ml of 25% sulphuric acid. After 20 minutes, the mixture is made alkaline with 10% sodium bicarbonate solution and extracted several times with methylene chloride. The methylene chloride solution is dried over sodium sulphate, filtered and concentrated. The residue is purified on a 80 g silica gel column using ethyl acetate as the eluting agent and recrystallised from ethyl acetate. There is obtained 1-(2-tert.butoxyethyl)-3-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]urea which melts at 177° C.

Workup

extractionextracted several times with methylene chloride
dry with materialThe methylene chloride solution is dried over sodium sulphate
filtrationfiltered
concentrationconcentrated
customThe residue is purified on a 80 g silica gel column
customrecrystallised from ethyl acetate

Sources & evidence

ORD record: ord-7b8b5b7c3fc244e08624885597449b4b
Source dataset: uspto-grants-1981_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04294758

Reaction notes

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