Thiophosgene → HCID 18942727, compound

HRID 2081161Notes

Reaction equation

HRID 2081161 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([B:11]([OH:13])[OH:12])[CH:5]=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1.[C:14](Cl)(Cl)=[S:15]>Cl>[N:1]([C:2]1[CH:3]=[C:4]([B:11]([OH:13])[OH:12])[CH:5]=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1)=[C:14]=[S:15]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 27377953-Amino-5-carboxybenzeneboronic acid

Product 1

HCID 18942727HCID 18942727, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of 3-amino-5-carboxyphenylboronic acid (150 mg, 0.08 mmol) in 3N HCl (3 ml) was added thiophosgene (92 mg, 0.08 mmol) in 3N HCl (3 ml) and the reaction mixture was stirred at room temperature. A white solid was formed after 20 minutes. This was recrystallized from hexane/ethyl acetate. M.P. >350° C. Anal. Calcd. for C8H6NO4BS.3H2O. C, 42.06; H, 2.91; N, 6.13. Found: C, 42.51; H, 2.87; N, 5.68.

Workup

  1. customA white solid was formed after 20 minutes
  2. customThis was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-c4a5c0fb8a5b443d9f0ee28be40ea650
Source dataset
uspto-grants-1993_02
Patent number
US05183653

Reaction notes

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