Sodium Iodide → HCID 135529009, compound

HRID 1531674Notes

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:41])[C:31]3[C:36]([O:37][CH3:38])=[CH:35][CH:34]=[CH:33][C:32]=3[O:39][CH3:40])=[CH:13][CH:14]=2)[CH:9]=1)(=[O:7])=[O:6])(C)C.[I-].[Na+]>CC(=O)CC>[CH3:38][O:37][C:36]1[CH:35]=[CH:34][CH:33]=[C:32]([O:39][CH3:40])[C:31]=1[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:4])=[O:6])=[CH:9]2)=[CH:14][CH:13]=1)=[O:41]

Participants

Conditions

Temperature: 60 °C

Procedure

7-(2,6-Dimethoxy-benzoylamino)-4-hydroxy-3-(4-methoxy-phenylazo)-napthalene-2-sulfonic acid isopropyl ester (Example 17, 35 mg, 0.06 mmol) was suspended in 2-butanone (3 m) and sodium iodide (18 mg, 0.12 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 (30 mg, 0.053 mmol, 89%) as a red solid: NMR (DMSO-d6): δ 16.38 (s, 1H), 10.71 (s, 1H), 8.35 (d, J=9 Hz, 1H), 8.11 (s, 1H), 7.90 (m, 3H), 7.52 (s, 1H), 7.44 (t, J=9 Hz, 1H), 7.07 (d, J=9 Hz, 2H), 6.67 (d, J=9 Hz, 2H), 3.92 (s, 3H), 3.87 (s, 6H); Analytical HPLC: 87% pure; MS (ES-NEG): [M−H] 536; Anal. Calc. for C26H23N3O8SNa: C, 55.81, H, 3.96, N, 7.51. Found: C, 50.83, H, 4.07, N, 6.42.

Workup

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

Sources & evidence

ORD record: ord-fadf85b3734c48329d775383a41ba629
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200963B1

Reaction notes

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