Sodium Hydroxide → HCID 23452282, compound

HRID 1277912Notes

Reaction equation

HRID 1277912 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[OH-].[Na+].[I:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13]>O.O1CCCC1>[I:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](=[O:13])[NH:2][CH2:3][C:4]([NH2:6])=[O:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 691122-Iodobenzoyl chlorideHCID 2723639Glycinamide hydrochloride

Product 1

HCID 23452282HCID 23452282, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.0 g of glycinamide hydrochloride in 10 ml of water was cooled in an ice bath during the addition of 30 ml of 6 N sodium hydroxide. To the resulting mixture was added a solution of 8.0 g o-iodobenzoyl chloride in 20 ml of tetrahydrofuran and the mixture was shaken vigorously for 2 minutes. The mixture was then stirred for 21/2 hours. The tan solid which formed was filtered by suction and washed with water until the washings were neutral. The residue was then dried on a rotary evaporator for 5 hours at 60° and 80 mm Hg. There was thus obtained a crude product which was recrystallized from ethanol to yield 2.0 g of o-iodohippuramide as buff colored crystals, m.p. 183°-185°, Rf 0.64.

Workup

  1. stirringThe mixture was then stirred for 21/2 hours
  2. customThe tan solid which formed
  3. filtrationwas filtered by suction
  4. washwashed with water until the washings
  5. customThe residue was then dried on a rotary evaporator for 5 hours at 60°
  6. customThere was thus obtained a crude product which
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-3deee871853b4614b26d7b5a28e2a346
Source dataset
uspto-grants-1981_07
Patent number
US04279887

Reaction notes

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