HCID 12595979, compound → HCID 12595984, compound

HRID 1701284Notes

Reaction equation

HRID 1701284 reaction equation
[NH2:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[CH2:4][N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10](O)=[O:11].NC1C=C(Cl)C=CC=1CN1C=CC=C1C#N>O1CCCC1>[Cl:17][C:15]1[CH:14]=[CH:13][C:3]2[CH2:4][N:5]3[CH:9]=[CH:8][CH:7]=[C:6]3[C:10](=[O:11])[NH:1][C:2]=2[CH:16]=1

Participants

4

Reactant 2

HCID 12595979HCID 12595979, compoundHCID 12595982HCID 12595982, compound

Product 1

HCID 12595984HCID 12595984, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 5.7 g. of 1-(2-amino-4-chlorobenzyl)-2-pyrrolecarboxylic acid (prepared by the method of Example 5, using 1-(2-amino-4-chlorobenzyl)-2-pyrrolecarbonitrile), 3.9 g. of N,N'-carbonyldiimidazole and 60 ml. of tetrahydrofuran is stirred with cooling for one hour, allowed to stand at room temperature, heated on a steam bath for one hour, diluted with 5 ml. of water and concentrated to remove the tetrahydrofuran. The residue is dissolved in methylene chloride, washed successively with water, 25 ml. of 1 N sodium hydroxide and water, dried over magnesium sulfate and concentrated to remove the solvent. The resulting viscous oil is dissolved in 20 ml. of ethyl acetate and cooled giving crystals. These crystals are heated at 105° C. for one hour and then triturated with ethyl acetate giving 8-chloro-5,10-dihydro-11H-pyrrolo[2,1-c][1,4]-benzodiazepin-11-one.

Workup

  1. additionA mixture of 5.7 g
  2. temperaturewith cooling for one hour
  3. customto stand at room temperature
  4. temperatureheated on a steam bath for one hour
  5. additiondiluted with 5 ml
  6. concentrationof water and concentrated
  7. customto remove the tetrahydrofuran
  8. dissolutionThe residue is dissolved in methylene chloride
  9. washwashed successively with water, 25 ml
  10. dry with materialof 1 N sodium hydroxide and water, dried over magnesium sulfate
  11. concentrationconcentrated
  12. customto remove the solvent
  13. dissolutionThe resulting viscous oil is dissolved in 20 ml
  14. temperatureof ethyl acetate and cooled
  15. customgiving crystals
  16. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-02c9f32d02a84b858ea8906278dfd1a4
Source dataset
uspto-grants-1980_03
Patent number
US04192803

Reaction notes

Loading…