Sodium Iodide → HCID 135529010, compound

HRID 1531670Notes

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[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[C:33]([O:39][CH3:40])[CH:32]=3)=[CH:13][CH:14]=2)[CH:9]=1)(=[O:7])=[O:6])(C)C.[I-].[Na+]>CC(=O)CC>[CH3:38][O:37][C:35]1[CH:36]=[C:31]([CH:32]=[C:33]([O:39][CH3:40])[CH:34]=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-(3,5-Dimethoxy-benzoylamino)-4-hydroxy-3-(4-methoxy-phenylazo)-napthalene-2-sulfonic acid isopropyl ester (Example 13, 96 mg, 0.19 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 (86 mg, 0.17 mmol, 91%) as a red solid: NMR (DMSO-d6): δ 16.34 (s, 1H), 10.47 (s, 1H), 8.27 (d, 9 Hz, 1H), 8.18 (m, 1H), 7.95 (d, J=9 Hz, 1H), 7.83 (d, J=9 Hz, 2H), 7.51 (s, 1H), 7.17 (d, J=3 Hz, 2H), 7.08 (d, J=9 Hz, 2H), 6.74 (t, J=2 Hz, 1H), 3.78 (m, 9H); Analytical HPLC: 94% pure; MS (ES-NEG): [M−H] 536; Anal. Calc. for C26H23N3O8SNa: C, 55.81, H, 3.96, N, 7.51. Found: C, 52.65, H, 4.45, N, 5.99.

Workup

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

Sources & evidence

ORD record: ord-069b84efa8eb4bb795b991e553f45ddd
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200963B1

Reaction notes

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