Ethyl isocyanate → Urea, N-(6-chloro-5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-N(sup 1)-ethyl-

HRID 1413779Notes

Reaction equation

HRID 1413779 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].[CH2:23]([N:25]=[C:26]=[O:27])[CH3:24]>>[Cl:22][C:21]1[C:6]2[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])=[N:8][CH2:9][C:10](=[O:13])[N:11]([CH3:12])[C:5]=2[CH:4]=[CH:3][C:2]=1[NH:1][C:26]([NH:25][CH2:23][CH3:24])=[O:27]

Participants

3

Reactant 2

HCID 8022Ethyl isocyanateHCID 20562334HCID 20562334, compound

Product 1

HCID 3058277Urea, N-(6-chloro-5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-N(sup 1)-ethyl-

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 are heated at reflux with 15 ml of ethylisocyanate under nitrogen for 7 hours. The mixture is poured on to methanol/ice-water and extracted 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 ethyl acetate as the eluting agent and crystallised from ethyl acetate/ether. There is obtained 1-[6-chloro-5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-ethylurea which melts at 155°-160° C. with decomposition.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic phase is separated
  3. dry with materialdried with sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified on a 300 g silica gel column
  7. customcrystallised from ethyl acetate/ether

Sources & evidence

ORD record
ord-0df25d3cff9642e880f9dbf3c17167c4
Source dataset
uspto-grants-1981_02
Patent number
US04251443

Reaction notes

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