Diethyl Ether → 7-Bromo-5-(2'-chloro-phenyl)-1,3-dihydro-1-methyl-3-[N-methyl-N-(morpholinocarbonyl-methyl)-amino-methylene]-2H-1,4-benzodiazepin-2-one

HRID 1076392Notes

Reaction equation

HRID 1076392 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9](=[CH:14][N:15]([CH3:17])[CH3:16])[N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:6]=2[CH:25]=1.O1CCCC1.CCOCC.N(C[C:39]([N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1)=[O:40])C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9](=[CH:14][N:15]([CH3:16])[CH2:17][C:39]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)=[O:40])[N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:6]=2[CH:25]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 25176834-((Methylamino)acetyl)morpholineHCID 544817197-bromo-5-(2'-chlorophenyl)-1,3-dihydro-3-(dimethylamino-methylene)-1-methyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 540346697-Bromo-5-(2'-chloro-phenyl)-1,3-dihydro-1-methyl-3-[N-methyl-N-(morpholinocarbonyl-methyl)-amino-methylene]-2H-1,4-benzodiazepin-2-one

Conditions

Temperature
160 °C

Procedure

A suspension of 8.4 gm of 7-bromo-5-(2'-chlorophenyl)-1,3-dihydro-3-(dimethylamino-methylene)-1-methyl-2H-1,4-benzodiazepin-2-one in 45 gm of sarcosine morpholide was heated to 160°C, while stirring, whereby a clear solution was formed after some time, which was stirred for 90 minutes more at 160°C. Thereafter, the reaction mixture was allowed to cool and was then taken up in a mixture consisting of 150 ml each of tetrahydrofuran and ether. The resulting solution was washed three times with 100 ml of water each, and the organic phase was dried over magnesium sulfate and evaporated in vacuo. The residue was purified on a silicagel column, using a 19:1-mixture of chloroform and methanol as the flow agent. Those fractions containing the desired compound were combined, the solvent mixture was distilled off in vacuo, and the residue was recrystallized from tetrahydrofuran, yielding the compound of the formula ##SPC8##

Workup

  1. customwhereby a clear solution was formed after some time, which
  2. stirringwas stirred for 90 minutes more at 160°C
  3. temperatureto cool
  4. washThe resulting solution was washed three times with 100 ml of water each, and the organic phase
  5. dry with materialwas dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified on a silicagel column
  8. additionThose fractions containing the desired compound
  9. distillationthe solvent mixture was distilled off in vacuo
  10. customthe residue was recrystallized from tetrahydrofuran
  11. customyielding the compound of the formula

Sources & evidence

ORD record
ord-d6f7187d2ac040cf8e0618fa45487388
Source dataset
uspto-grants-1976_05
Patent number
US03956492

Reaction notes

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