Sodium Hydroxide → 3-Carbamoyl-2,4,6-triiodophenoxyacetic acid

HRID 2296498Notes

Reaction equation

HRID 2296498 reaction equation
[C:1]([C:3]1[C:4]([I:16])=[C:5]([C:11]([I:15])=[CH:12][C:13]=1[I:14])[O:6][CH2:7][C:8]([OH:10])=[O:9])#[N:2].[OH-:17].[Na+]>>[C:1]([C:3]1[C:4]([I:16])=[C:5]([C:11]([I:15])=[CH:12][C:13]=1[I:14])[O:6][CH2:7][C:8]([OH:10])=[O:9])(=[O:17])[NH2:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 198483643-Cyano-2,4,6-triiodophenoxyacetic acid

Product 1

HCID 198483573-Carbamoyl-2,4,6-triiodophenoxyacetic acid

Procedure

27.3 g (49 mmol) of 3-cyano-2,4,6-triiodophenoxyacetic acid is stirred in 100 ml of 2 N sodium hydroxide solution for 3 hours at 50° C. The resultant alkaline solution is filtered over active carbon for purifying and decolorizing and then brought to pH 2 by adding 2 N hydrochloric acid. After several hours of stirring in an ice bath, the yield is 23.9 g (85% of theory) of 3-carbamoyl-2,4,6-triiodophenoxyacetic acid as a white powder, mp 211°-213° C. (decomposition).

Workup

  1. filtrationThe resultant alkaline solution is filtered over active carbon
  2. customfor purifying
  3. additionby adding 2 N hydrochloric acid

Sources & evidence

ORD record
ord-68dc077017934ed097aa92ab032e2c1f
Source dataset
uspto-grants-1984_01
Patent number
US04429152

Reaction notes

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