Water → HCID 70456073, compound

HRID 280613Notes

Reaction equation

HRID 280613 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[C:8]([C:11]#N)[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:13][C:14]1[NH:15][CH:16]=[CH:17][N:18]=1.[OH-:19].[Na+].[OH2:21]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:6]2[CH:7]=[C:8]([C:11]([OH:21])=[O:19])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:13][C:14]1[NH:15][CH:16]=[CH:17][N:18]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 70456055HCID 70456055, compound

Product 1

HCID 70456073HCID 70456073, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3-chloro-2-(1-imidazolylmethyl)benzofuran-5-carbonitrile (0.35 g) in concentrated sulphuric acid (5 ml) and water (5 ml) was heated under reflux for 1 hour and then cooled. The solution was diluted with 5 ml of water and made just alkaline by the addition of 5N sodium hydroxide solution. The solution was filtered and made acidic by the addition of acetic acid. The solid which crystallised out on standing was filtered off, washed with water and dried to give 3-chloro-2-(1-imidazolylmethyl)benzofuran-5-carboxylic acid (0.20 g), m.p. 248°-250°.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturecooled
  3. filtrationThe solution was filtered
  4. additionmade acidic by the addition of acetic acid
  5. customThe solid which crystallised out on standing
  6. filtrationwas filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-30941034036d4341ac391c961125b5b2
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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