Chloroacetonitrile → HCID 14116886, compound

HRID 1086032Notes

Reaction equation

HRID 1086032 reaction equation
[H-].[Na+].Cl.[NH2:4][C:5]1[C:20]([Cl:21])=[CH:19][C:8]([C:9]([NH:11][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:10])=[C:7]([OH:22])[CH:6]=1.Cl[CH2:24][C:25]#[N:26].[Br-].[Na+]>CN(C=O)C.C(Cl)Cl.O>[NH2:4][C:5]1[C:20]([Cl:21])=[CH:19][C:8]([C:9]([NH:11][CH2:12][CH2:13][N:14]([CH2:15][CH3:16])[CH2:17][CH3:18])=[O:10])=[C:7]([O:22][CH2:24][C:25]#[N:26])[CH:6]=1

Participants

8

Reactant 4

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 253881Sodium BromideHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

Product 1

HCID 14116886HCID 14116886, compoundYield 57.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of sodium hydride (420 mg of 60%, 10.5 mmoles, washed with n-pentane) in 10 ml DMF was added 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (1.612 g, 5 mmoles) and the mixture stirred for 20 minutes, followed by cooling (ice bath) and addition of chloroacetonitrile (418 mg, 5.5 mmoles) and sodium bromide (100 mg). The mixture was stirred in the cold for 1 hour and at ambient temperature for 16 hours, followed by pouring into a mixture of water and ice, and filtration of the resulting solid. The product was dissolved in methylene chloride and filtered over alumina, followed by concentration in vacuo to give crude product. This was recrystallized from methanol to give 930 mg (57%) of the title compound as white crystalline solid mp 188°-189°. The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ 8.1 (s, 1H); 7.78 (bs, 1 H); 6.44 (s, 1H); 4.84 (s, 2H); 4.60 (s, 2H); 3.43 (m, 2H); 2.59 (m, 6H); 1.02 (t, 6H).

Workup

  1. temperatureby cooling
  2. stirringThe mixture was stirred in the cold for 1 hour
  3. waitat ambient temperature for 16 hours
  4. filtrationfiltered over alumina
  5. concentrationfollowed by concentration in vacuo
  6. customto give crude product
  7. customThis was recrystallized from methanol

Sources & evidence

ORD record
ord-c42ef2cb36a845cc866f3b11910f2bae
Source dataset
uspto-grants-1991_04
Patent number
US05011992

Reaction notes

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