Ammonia → 3-fluoro-5-o-fluorophenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one

HRID 224368

Reaction equation

HRID 224368 reaction equation
N.C1N2CN3CN(C2)C[N:3]1C3.Br[CH:13]([F:35])[C:14]([NH:16][C:17]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][C:18]=1[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27])=O)=[O:15].NC1C=CC([N+]([O-])=O)=CC=1C(C1C=CC=CC=1F)=O.BrC(F)C(Br)=O>C(O)C>[F:35][CH:13]1[N:3]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[C:18]2[CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[CH:30]=[CH:31][C:17]=2[NH:16][C:14]1=[O:15]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 4101HexamethylenetetramineHCID 676572-Amino-2'-fluoro-5-nitrobenzophenoneHCID 233326402-(alpha-Bromo-alpha-fluoroacetamido)-5-nitro-2'-fluorobenzophenoneHCID 23332663alpha-Bromo-alpha-fluoroacetyl bromide

Product 1

HCID 233325603-fluoro-5-o-fluorophenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NH3 is passed into a refluxing solution of 1.48 g. of hexamethylenetetramine in 30 ml. of ethanol; 3.83 g. of 2-(α-bromo-α-fluoroacetamido)-5-nitro-2'-fluorobenzophenone, obtainable from 2-amino-5-nitro-2'-fluorobenzophenone and α-bromo-α-fluoroacetyl bromide, are added over 2 hours. The mixture is then heated under reflux for 3 hours more and is evaporated. The resulting 2-(α-amino-α-fluoroacetamido)-5-nitro-2'-fluorobenzophenone is treated with 15 ml. of toluene and 20 mg. of p-tolunesulfonic acid and is heated under reflux for 1 hour. Working up in the customary manner gives 3-fluoro-5-o-fluorophenyl-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 3 hours more
  3. customis evaporated
  4. additionThe resulting 2-(α-amino-α-fluoroacetamido)-5-nitro-2'-fluorobenzophenone is treated with 15 ml
  5. temperatureof p-tolunesulfonic acid and is heated
  6. temperatureunder reflux for 1 hour

Sources & evidence

ORD record
ord-5b5b4ec6a18646e5ada4fff703b054be
Source dataset
uspto-grants-1980_11
Patent number
US04232016

Linked notes

Loading…