Hydrochloric Acid → 112918-82-8

HRID 1073068Notes

Reaction equation

HRID 1073068 reaction equation
[NH:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4].[CH:10]1[CH:15]=[C:14]2[CH:16]([CH2:23][O:24][C:25](Cl)=[O:26])[C:17]3[C:22]([C:13]2=[CH:12][CH:11]=1)=[CH:21][CH:20]=[CH:19][CH:18]=3.Cl>C(=O)(O)[O-].[Na+].CC(C)=O.[Cl-].[Na+].O>[C:25]([N:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4])([O:24][CH2:23][CH:16]1[C:14]2[C:13](=[CH:12][CH:11]=[CH:10][CH:15]=2)[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:26]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8897Iminodiacetic acidHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 601361112918-82-8

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 516892Sodium BicarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Iminodiacetic acid (2.19 g, 16.5 mmol, Sigma Chemical Co., St. Louis, Mo.) was dissolved in a mixture of 1 M sodium bicarbonate (40 ml) and acetone (30 ml). 9-Fluorenemethyl chloroformate (2.0 g, 7.7 mmol) was dissolved in acetone (10 ml) and added to the above solution. After 6 hours reaction, the mixture was treated with brine, acidified with 1N HCl, and extracted with ethyl acetate. The yield was 2.38 g (87%), mp 213°-215.5° C. The mass spectrum (CI-NH3) showed a peak at 373 corresponding to m+1+NH3. Analysis (C19H17N06): calc. 64.22% C, 4.82% H, 3.94% N; found 64.15% C, 4.83% H, 3.909% N.

Workup

  1. additionadded to the above solution
  2. customAfter 6 hours reaction
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-2ef805e5625044fdaa10ae489b87f2c8
Source dataset
uspto-grants-1990_11
Patent number
US04968672

Reaction notes

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