Ethanol → HCID 20562369, compound

HRID 848547Notes

Reaction equation

HRID 848547 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[C:21]=1[Cl:22].[Cl:23][CH2:24][CH2:25][N:26]=[C:27]=[O:28].C(N(CC)CC)C.C(O)C>O1CCCC1>[Cl:23][CH2:24][CH2:25][NH:26][C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[C:21]=1[Cl:22])=[O:28]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 20562334HCID 20562334, compound

Product 1

HCID 20562369HCID 20562369, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 g (0.016 M) of 7-amino-6-chloro-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one in 85 ml of absolute tetrahydrofuran are treated with 11.1 ml of chloroethylisocyanate and 1 ml of triethylamine. The mixture is stirred at room temperature for 1 week and heated at reflux for 5 hours. The mixture is treated with 50 ml of ethanol and concentrated. The residue is treated with methylene chloride/water and extracted several times with methylene chloride. The organic phase is separated, dried with sodium sulphate, filtered and concentrated. The residue is purified on a 300 g silica gel column using methylene chloride/ethyl acetate (3:1) as the eluting agent, there being obtained 1-(2-chloroethyl)-3-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]urea which is further processed directly.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. concentrationconcentrated
  4. additionThe residue is treated with methylene chloride/water
  5. extractionextracted several times with methylene chloride
  6. customThe organic phase is separated
  7. dry with materialdried with sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue is purified on a 300 g silica gel column

Sources & evidence

ORD record
ord-4b1f2ff5836e4917823d0adbc894f346
Source dataset
uspto-grants-1981_10
Patent number
US04296031

Reaction notes

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