Ammonia → RO-05-2921

HRID 1973067

Reaction equation

HRID 1973067 reaction equation
C(O)C.C1N2CN3CN(C2)C[N:5]1C3.N.Cl[CH2:16][C:17]([NH:19][C:20]1[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=1[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=O)=[O:18]>C(Cl)(Cl)Cl>[C:24]1([C:22]2[C:21]3[CH:30]=[CH:31][CH:32]=[CH:33][C:20]=3[NH:19][C:17](=[O:18])[CH2:16][N:5]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 702EthanolHCID 4101HexamethylenetetramineHCID 2064069N-(2-benzoylphenyl)-2-chloroacetamide

Product 1

HCID 76175RO-05-2921Yield 86%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of ethanol (300 ml) and hexamethylenetetramine (20 g., 0.143 mol) was stirred, heated to reflux, and saturated with ammonia. 2-Chloroacetamidobenzophenone (18.1 g., 0.066 mol) was added in small increments over 3 to 4 hours while a steady stream of ammonia was bubbled into the reaction mixture. Refluxing was continued for 3 hours after complete addition of 2-chloroacetamidobenzophenone. The flow of ammonia was interrupted and the ethanol removed by distillation in vacuo. The residue obtained was taken up in chloroform (200 ml), and washed with water (100 ml) at 50° C. The chloroform layer was evaporated to dryness at 30° C. and the oily solid obtained was recrystallized from toluene (100 ml) to give 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (13.2 g., 86%), melting at 184°-186° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customwas bubbled into the reaction mixture
  4. temperatureRefluxing
  5. additionafter complete addition of 2-chloroacetamidobenzophenone
  6. customthe ethanol removed by distillation in vacuo
  7. customThe residue obtained
  8. washwashed with water (100 ml) at 50° C
  9. customThe chloroform layer was evaporated to dryness at 30° C.
  10. customthe oily solid obtained
  11. customwas recrystallized from toluene (100 ml)

Sources & evidence

ORD record
ord-a8b74999058a436a995fac845a405bd5
Source dataset
uspto-grants-1976_12
Patent number
US03996209

Linked notes

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