Thiophosgene → Isothiocyanobenzyl EDTA

HRID 621763

Reaction equation

HRID 621763 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH:7]([N:18]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][C:20]([OH:22])=[O:21])[CH2:8][N:9]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[C:34](Cl)(Cl)=[S:35].C1C=CC(C2C(=O)C3(OC(=O)C4C3=CC=CC=4)OC=2)=CC=1>O.C(Cl)(Cl)Cl>[N:1]([C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH:7]([N:18]([CH2:19][C:20]([OH:22])=[O:21])[CH2:23][C:24]([OH:26])=[O:25])[CH2:8][N:9]([CH2:10][C:11]([OH:13])=[O:12])[CH2:14][C:15]([OH:17])=[O:16])=[CH:4][CH:3]=1)=[C:34]=[S:35]

Participants

7

Reactant 4

HCID 10040ThiophosgeneHCID 37927FluorescamineHCID 134715Aminobenzyl-EDTAHCID 516892Sodium Bicarbonate

Product 1

HCID 5159032Isothiocyanobenzyl EDTA

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

The precursor 5 (0.33 mmol) was taken up in H2O (10 ml) and stirred rapidly in a 10 ml round bottom flask fitted with an addition funnel. The pH was adjusted to 8.5 with solid NaHCO3 and thiophosgene (42 mg, 0.365 mmol) in CHCl3 (10 ml) was added dropwise. Stirring was continued until the solution tested negative for amine by the fluorescamine method. The aqueous layer was taken to dryness. Purification was done by column chromatography on a 1×30 cm Florisil™ column eluted with acetonitrile:water (30:8). The product eluted from the column cleanly as determined by TLC and was stored in a dessicator in a freezer and re-purified immediately prior to use.

Workup

  1. customfitted with an addition funnel
  2. additionwas added dropwise
  3. stirringStirring
  4. customPurification
  5. washeluted with acetonitrile:water (30:8)
  6. washThe product eluted from the column cleanly
  7. customre-purified immediately

Sources & evidence

ORD record
ord-0c35635aa2a840e98d4bcbaa04fb2a84
Source dataset
uspto-grants-1989_04
Patent number
US04824986

Linked notes

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