Dimethylformamide → HCID 20335781, compound

HRID 2420478Notes

Reaction equation

HRID 2420478 reaction equation
[O:1]=[C:2]1[N:6]2[C:7]3[CH:22]=[CH:21][C:20]([Cl:23])=[N:19][C:8]=3[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])=[N:10][CH2:11][CH:5]2[NH:4][NH:3]1.CN(C)C=O.[H-].[Na+].Cl[CH2:32][C:33]#[N:34]>C(Cl)(Cl)Cl.O>[O:1]=[C:2]1[N:6]2[C:7]3[CH:22]=[CH:21][C:20]([Cl:23])=[N:19][C:8]=3[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])=[N:10][CH2:11][C:5]2=[N:4][N:3]1[CH2:32][C:33]#[N:34]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 20335747HCID 20335747, compound

Product 1

HCID 20335781HCID 20335781, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

20 grams of 1-keto-6-(o-chlorophenyl)-8-chloro-1,3-dihydro-4H-s-triazolo-(4,3-a)-pyrido-(2,3-f)-(1,4)-diazepine were dissolved in 100 ml. of dimethyl formamide, 1.8 grams of sodium hydride (about 80%) added with cooling, further stirred for 5 minutes, then 5 grams of chloroacetonitrile added (the temperature increased from 30° C. to about 50° C.) and stirring continued for 30 minutes. Then it was poured into about 1 liter of water, shaken with chloroform, the chloroform paste washed with dilute aqueous sodium hydroxide and subsequently with water, dried, suction filtered over a silica gel layer and evaporated. The chloroform residue crystallized upon triturating with methanol and was recrystallized from methanol. M.P. 198°-200° C.; Yield 8 grams.

Workup

  1. temperaturewith cooling
  2. temperatureincreased from 30° C. to about 50° C.) and
  3. stirringstirring
  4. waitcontinued for 30 minutes
  5. washthe chloroform paste washed with dilute aqueous sodium hydroxide and subsequently with water
  6. customdried
  7. filtrationsuction filtered over a silica gel layer
  8. customevaporated
  9. customThe chloroform residue crystallized
  10. customupon triturating with methanol
  11. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-8591d95b68f04313a868d55c62adaa98
Source dataset
uspto-grants-1978_08
Patent number
US04110455

Reaction notes

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