Chloroacetyl chloride → HCID 21525527, compound

HRID 1658766Notes

Reaction equation

HRID 1658766 reaction equation
[Br:1][C:2]1[C:3]([Br:18])=[CH:4][C:5]2[NH:11][C:10]3[N:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8](=[O:16])[NH:7][C:6]=2[CH:17]=1.[Cl:19][CH2:20][C:21](Cl)=[O:22].C(N(CC)CC)C>O>[Cl:19][CH2:20][C:21]([N:11]1[C:5]2[CH:4]=[C:3]([Br:18])[C:2]([Br:1])=[CH:17][C:6]=2[NH:7][C:8](=[O:16])[C:9]2[CH:15]=[CH:14][CH:13]=[N:12][C:10]1=2)=[O:22]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 21525560HCID 21525560, compound

Product 1

HCID 21525527HCID 21525527, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

6,11-Dihydro-8,9-dibromo-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one (0.1 mol) in 300 ml. of water-free dioxane is dissolved by heating to reflux. To the boiling solution is added, dropwise over 30 minutes, a solution of 15. g. (0.14 mol) of chloroacetyl chloride, dissolved in 40 ml. of water-free dioxane, and simultaneously 14.4 (0.14 mol) of triethylamine, dissolved in 30 ml. of water-free dioxane. The mixture is refluxed for 8 hours and then filtered while hot. The filtrate is evaporated in vacuo, and the resulting residue is recrystallized from acetonitrile to give 11-chloroacetyl-8,9-dibromo-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one.

Workup

  1. temperatureby heating to reflux
  2. additionTo the boiling solution is added, dropwise over 30 minutes
  3. temperatureThe mixture is refluxed for 8 hours
  4. filtrationfiltered while hot
  5. customThe filtrate is evaporated in vacuo
  6. customthe resulting residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-997593bc1f464600b99b6fa900816d23
Source dataset
uspto-grants-1976_06
Patent number
US03966736

Reaction notes

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