4-Iodobenzoic acid → N-{2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-4-iodo-benzamide

HRID 1174986Notes

Reaction equation

HRID 1174986 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:17][N:18]([CH3:33])[CH2:19][CH2:20][N:21]([CH3:32])[C:22]1[S:23][C:24]2[CH:30]=[C:29]([NH2:31])[CH:28]=[CH:27][C:25]=2[N:26]=1>>[CH3:17][N:18]([CH3:33])[CH2:19][CH2:20][N:21]([CH3:32])[C:22]1[S:23][C:24]2[CH:30]=[C:29]([NH:31][C:6](=[O:8])[C:5]3[CH:4]=[CH:3][C:2]([I:1])=[CH:10][CH:9]=3)[CH:28]=[CH:27][C:25]=2[N:26]=1

Participants

4

Reactant 3

HCID 120854-Iodobenzoic acidHCID 65578Oxalyl chlorideHCID 55226563N2-(2-Dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamine

Product 1

HCID 57771748N-{2-[(2-dimethylamino-ethyl)-methyl-amino]-benzothiazol-6-yl}-4-iodo-benzamide

Procedure

The title compound is prepared by following Method C, using 4-iodo-benzoic acid (4.46 g, 17.97 mmol), oxalyl chloride (5.2 mL, 59.11 mmol) and N*2*-(2-dimethylamino-ethyl)-N*2*-methyl-benzothiazole-2,6-diamine (3.0 g, 11.98 mmol) to afford 3.77 g, 66%). LC/MS, Retention time=5.62 min; (m/z): calcd for C19H211N4OS: 480.4; found: 480.7.

Workup

  1. customto afford 3.77 g, 66%)

Sources & evidence

ORD record
ord-9fdbf1ffc8da4610b9e23acee4402837
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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