Pyridine → HCID 20393037, compound

HRID 1862972Notes

Reaction equation

HRID 1862972 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH3:5][C:6]1[CH:7]=[C:8]([CH3:23])[C:9]2[C:15](=[O:16])[N:14]([CH3:17])[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=3[NH:11][C:10]=2[N:22]=1.C(C(CC)=O)C.N1C=CC=CC=1>C1(C)C=CC=CC=1.O>[Cl:4][C:1]([N:11]1[C:12]2[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=2[N:14]([CH3:17])[C:15](=[O:16])[C:9]2[C:8]([CH3:23])=[CH:7][C:6]([CH3:5])=[N:22][C:10]1=2)=[O:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 7288Ethyl ketoneHCID 20393030HCID 20393030, compound

Product 1

HCID 20393037HCID 20393037, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
110 °C

Procedure

50 ml of a 20% solution of phosgene in toluene were added dropwise over a period of 10 minutes to a mixture consisting of 10.0 gm of 6,11-dihydro-2,4,6-trimethyl-5H-pyrido[2,3-b][1,5]-benzodiazepin-5-one, 100 ml of diethyl ketone, 50 ml of toluene and 5 ml of pyridine. The resulting mixture was heated at 60° C. for 2 hours, at 80° C. for one hour and at 110° C. for one hour, while stirring. After cooling to room temperature, 100 ml of water were added. The organic phase was dried with sodium sulfate and then evaporated in vacuo. The residue was recrystallized twice from ethanol, yielding 7.3 gm of 11-chloroformyl-6,11-dihydro-2,4,6-trimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, m.p. 205°-207° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was recrystallized twice from ethanol

Sources & evidence

ORD record
ord-00f7ed3dd2724bccbdf5fd750d869694
Source dataset
uspto-grants-1979_09
Patent number
US04167570

Reaction notes

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