Sodium Iodide → HCID 135528950, compound

HRID 1531672Notes

Reaction equation

HRID 1531672 reaction equation
C([O:4][S:5]([C:8]1[C:17]([N:18]=[N:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:16]([OH:28])[C:15]2[C:10](=[CH:11][C:12]([NH:29][C:30](=[O:37])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:13][CH:14]=2)[CH:9]=1)(=[O:7])=[O:6])(C)C.[I-].[Na+]>CC(=O)CC>[C:30]([NH:29][C:12]1[CH:11]=[C:10]2[C:15]([C:16]([OH:28])=[C:17]([N:18]=[N:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[C:8]([S:5]([OH:7])(=[O:6])=[O:4])=[CH:9]2)=[CH:14][CH:13]=1)(=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 135544188HCID 135544188, compound

Product 1

HCID 135528950HCID 135528950, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

7-Benzoylamino-4-hydroxy-3-(4-methoxy-phenylazo-napthalene-2-sulfonic acid isopropyl ester (Example 15, 49 mg, 0.09 mmol) was suspended in 2-butanone (3 mL) and sodium iodide (57 mg, 0.38 mmol) was added. The reaction mixture was allowed to stir under nitrogen at 60° C. for 24 h. The solvent was removed under a stream of nitrogen, acetone was added and the suspension was filtered to provide the title compound (51 mg, 0.08 mmol, 91%) as a red solid: NMR (DMSO-d6): δ 16.30 (s, 1H), 10.68 (s, 1H), 8.26 (d, J=9 Hz, 1H), 8.19 (m, 1H), 8.01 (m, 3H), 7.83 (d, 4H), 7.10 (d, J=9 Hz, 2H), 3.92 (s, 3H); Analytical BPLC: 99% pure; MS (ES-NEG): [M−H] 476; Anal. Calc. for C27H25N3O6S: C, 57.71, H, 3.63, N, 8.41. Found: C, 52.85, H, 4.44, N, 6.66.

Workup

  1. customThe solvent was removed under a stream of nitrogen, acetone
  2. additionwas added
  3. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-b35625023e564300bd2cf9cbf1e74522
Source dataset
uspto-grants-2001_03
Patent number
US06200963B1

Reaction notes

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