Sodium Iodide → HCID 19778672, compound

HRID 2082469Notes

Reaction equation

[CH3:1][NH:2][CH2:3][CH:4]1[O:9][C:8]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:7]=2[O:6][CH2:5]1.Cl[CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][C:26](=[O:30])[O:27]2)=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>CN(C=O)C>[OH:14][C:12]1[CH:11]=[CH:10][C:8]2[O:9][CH:4]([CH2:3][N:2]([CH3:1])[CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]4[CH:24]=[CH:25][C:26](=[O:30])[O:27][C:28]=4[CH:29]=3)[CH2:5][O:6][C:7]=2[CH:13]=1

Participants

Conditions

Temperature: 96 °C

Procedure

N-Methyl-2,3-dihydro-6-hydroxy-1,4-benzodioxin-2-methanamine (3.68 g, 17.3 mmole), 7-(3-chloropropoxy)coumarin (4.15 g, 17.4 mmole), diisopropylethylamine (4.4 ml, 25.3 mmole) and sodium iodide (2.59 g, 17.3 mmole) were combined in 75 ml of DMF and heated at 96° C. for 26 hours under a nitrogen atmosphere. The solvent was then removed in vacuum and the residue was column chromatographed on silica gel using first 1% methanol/dichloromethane, then 2% methanol/dichloromethane as eluant. The product-containing fractions were combined and concentrated in vacuum and the residue crystallized from isopropanol with addition of 4N HCl/isopropanol and diethyl ether to give 1.71 g of white solid, monohydrochloride, quarter hydrate, m.p. 186°-193° C.

Workup

customThe solvent was then removed in vacuum
customchromatographed on silica gel using first 1% methanol/dichloromethane
concentrationconcentrated in vacuum
customthe residue crystallized from isopropanol with addition of 4N HCl/isopropanol and diethyl ether

Sources & evidence

ORD record: ord-e3d9e850830f48ebba4410196d556e7b
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05189171

Reaction notes

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