Phenol → HCID 54041040, compound

HRID 1154453Notes

Reaction equation

HRID 1154453 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](N3C=CN=C3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:27]1([OH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[C:7]2[C:8](=[O:26])[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 54332091(S)-1-[(8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl)carbonyl]imidazole

Product 1

HCID 54041040HCID 54041040, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.84 g (5 mmol) of (S)-1-[(8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl)carbonyl]imidazole, 0.56 g (6 mmol) of phenol, 0.83 g (6 mmol) of powdered potassium carbonate and 20 ml of dry dimethylformamide is stirred at room temperature for 26 hours, then poured into 100 ml of water and extracted three times with chloroform. The chloroform solution is washed twice with water and three times with saturated sodium chloride solution, dried over magnesium sulphate and evaporated. The crude product is purified by chromatography on silica gel while eluting with ethyl acetate and recrystallization from ethyl acetate. There is obtained phenyl (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 211°-212°.

Workup

  1. extractionextracted three times with chloroform
  2. washThe chloroform solution is washed twice with water and three times with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe crude product is purified by chromatography on silica gel
  6. washwhile eluting with ethyl acetate and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-7965af2eb6f94d33b6ec97a65e634b1c
Source dataset
uspto-grants-1984_12
Patent number
US04489003

Reaction notes

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