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Sodium Bicarbonate → Urea, N-(5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-N(sup 1)-(2-hydroxyethyl)-

HRID 848150
Notes
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Reaction equation

HRID 848150 reaction equation
C([O:4][CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]2[N:20]([CH3:21])[C:19](=[O:22])[CH2:18][N:17]=[C:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:15]=2[CH:30]=1)=[O:9])(=O)C.C[O-].[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C.C(Cl)Cl>[F:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:16]1[C:15]2[CH:30]=[C:11]([NH:10][C:8]([NH:7][CH2:6][CH2:5][OH:4])=[O:9])[CH:12]=[CH:13][C:14]=2[N:20]([CH3:21])[C:19](=[O:22])[CH2:18][N:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 20562331HCID 20562331, compound

Product 1

HCID 3058284Urea, N-(5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-N(sup 1)-(2-hydroxyethyl)-

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalyst
HCID 887
Methanol
Solvent
HCID 6344DichloromethaneSolvent

Procedure

20 mg (0.048 mM) of 2-[3-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]ethyl acetate are dissolved in 2 ml of absolute methanol and stirred at 30°-40° C. for 1 hour with 13 mg of sodium methylate. The mixture is then buffered with a few drops of glacial acetic acid, diluted with methylene chloride, treated with 10% sodium bicarbonate solution and extracted several times with methylene chloride. The organic phases are combined, dried over sodium sulphate, filtered and concentrated. The residue is crystallised from acetone/ether. There is obtained 1-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2-hydroxyethyl)urea which, according to the IR spectrum, is identical with a sample of this substance prepared in another manner (see Example 7).

Workup

  1. extractionextracted several times with methylene chloride
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is crystallised from acetone/ether

Sources & evidence

ORD record
ord-d7da8517db6e46b8b50534b6b701c38e
Source dataset
uspto-grants-1981_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04294758

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes