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

HRID 2308453Notes

Reaction equation

HRID 2308453 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-8049732708664dc7ab314270088a0b48
Source dataset
uspto-grants-2004_12
Patent number
US06835732B2

Reaction notes

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