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

HRID 848546
Notes
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Reaction equation

HRID 848546 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)C>CO>[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

5

Reactant 3

HCID 176Acetic AcidHCID 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 1

HCID 887MethanolSolvent

Procedure

300 mg (0.73 mM) of 2-[3-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]ethyl acetate dissolved in 20 ml of absolute methanol are treated with 500 mg of sodium methylate and stirred at room temperature for 1 hour. The mixture is then buffered with a small amount of acetic acid and concentrated. The residue is treated with methylene chloride/10% sodium bicarbonate solution, the aqueous solution is extracted several times with methylene chloride and the organic solution is dried over sodium sulphate, filtered and concentrated. After crystallisation from acetone, 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. concentrationconcentrated
  2. additionThe residue is treated with methylene chloride/10% sodium bicarbonate solution
  3. extractionthe aqueous solution is extracted several times with methylene chloride
  4. dry with materialthe organic solution is dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAfter crystallisation from acetone

Sources & evidence

ORD record
ord-8824a2db9947473dbdebdd810a879ceb
Source dataset
uspto-grants-1981_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04296031

Reaction notes

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