Acetic Acid → HCID 20335760, compound

HRID 2420479Notes

Reaction equation

HRID 2420479 reaction equation
[O:1]=[C:2]1[N:6]2[C:7]3[CH:26]=[CH:25][C:24]([Cl:27])=[N:23][C:8]=3[C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])=[N:10][CH:11]([O:12]C(=O)C)[C:5]2=[N:4][NH:3]1.C(O)CC.[OH-].[K+].C(O)(=O)C>O>[O:1]=[C:2]1[N:6]2[C:7]3[CH:26]=[CH:25][C:24]([Cl:27])=[N:23][C:8]=3[C:9]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])=[N:10][CH:11]([OH:12])[C:5]2=[N:4][NH:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10311-Propanol2×HCID 14797Potassium HydroxideHCID 20335774HCID 20335774, compound

Product 1

HCID 20335760HCID 20335760, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9 grams of 1-keto-4-acetoxy-6-(o-chlorophenyl)-8-chloro-1,2-dihydro-4H-s-triazolo-(4,3-a)-pyrido-(2,3-f)-(1,4)-diazepine were stirred with 60 ml. of n-propanol and a mixture of 10 grams of powdered potassium hydroxide and 100 ml. of n-propanol added. The mixture was stirred for 15 minutes at room temperature. Then it was acidified with glacial acetic acid and 600 ml. of water added. The reaction product crystallized out. It was filtered off with suction and then washed with water. The product can be recrystallized from dimethylformamide-ether whereupon it is subsequently boiled with ethanol for 30 minutes for the complete removal of the dimethyl formamide. Yield 5 grams; M.P. 260°-262° C.

Workup

  1. customThe reaction product crystallized out
  2. filtrationIt was filtered off with suction
  3. washwashed with water
  4. customThe product can be recrystallized from dimethylformamide-ether whereupon it
  5. customis subsequently boiled with ethanol for 30 minutes for the complete removal of the dimethyl formamide

Sources & evidence

ORD record
ord-2baf2dfcbb3d41d8a572a84d8649677b
Source dataset
uspto-grants-1978_08
Patent number
US04110455

Reaction notes

Loading…