Acetic Acid → HCID 13952845, compound

HRID 2118650Notes

Reaction equation

HRID 2118650 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][CH:8]([CH3:15])[CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)=[O:5].[N:21]([O-])=O.[Na+].[OH-].[Na+].C(O)(=O)C>O.Cl>[Cl:20][C:17]1[CH:18]=[CH:19][C:2]2[N:1]=[N:21][N:6]([CH2:7][CH:8]([CH3:15])[CH2:9][N:10]3[CH:14]=[CH:13][N:12]=[CH:11]3)[C:4](=[O:5])[C:3]=2[CH:16]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 13952745HCID 13952745, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13952845HCID 13952845, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 5.86 g of 2-amino-5-chloro-N-[3-(1H-imidazol-1-yl)-2-methylpropyl]benzamide in 30 ml of water and 8.3 ml of concentrated hydrochloric acid was cooled in an ice bath and a solution of 1.42 g of sodium nitrite in 10 ml of water was added dropwise. The mixture was stirred, treated for 50 minutes with 10 ml of 10N sodium hydroxide, stirred for 50 minutes and acetic acid was added until a pH of 6-7 was reached. The product was extracted into methylene chloride and the organic layer was washed with water, dried over magnesium sulfate and concentrated. Treatment with ethyl ether resulted in crystals of the desired product, mp 100°-102° C. A sample was converted to the hydrochloride salt, mp 185°-188° C.

Workup

  1. stirringstirred for 50 minutes
  2. extractionThe product was extracted into methylene chloride
  3. washthe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54c6eb389c9447f8a7bf78fcaf5cbcaa
Source dataset
uspto-grants-1987_07
Patent number
US04680293

Reaction notes

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