Iodine chloride → 5-Methyl-thiophene-2-carboxylic acid (4-methoxy-7-iodo-benzothiazol-2-yl)-amide

HRID 1062977Notes

Reaction equation

HRID 1062977 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:13]([C:15]3[S:16][C:17]([CH3:20])=[CH:18][CH:19]=3)=[O:14])[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[I:21]Cl.C([O-])(=O)C.[Na+].COC(=O)NC1SC2C=CC=C(OC)C=2N=1>C(O)(=O)C>[I:21][C:6]1[C:7]2[S:11][C:10]([NH:12][C:13]([C:15]3[S:16][C:17]([CH3:20])=[CH:18][CH:19]=3)=[O:14])=[N:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 21303403(4-Methoxy-benzothiazol-2-yl)-carbamic acid methyl esterHCID 360012145-Methyl-thiophene-2-carboxylic acid (4-methoxy-benzothiazol-2-yl)-amide

Product 1

HCID 865849065-Methyl-thiophene-2-carboxylic acid (4-methoxy-7-iodo-benzothiazol-2-yl)-amideYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Iodination of 5-methyl-thiophene-2-carboxylic acid (4-methoxy-benzothiazol-2-yl)-amide (5.17 g, 17 mmol) with iodine monochloride (2.26 ml, 44 mmol), sodium acetate (3.63 g, 44 mmol) and acetic acid (200 ml) in the same manner as described for (4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester affords the product as off-white solid in 93% yield. MS: m/e=430 (M+).

Sources & evidence

ORD record
ord-9c0ac871a8464558be98b32d0739b430
Source dataset
uspto-grants-2005_11
Patent number
US06963000B2

Reaction notes

Loading…