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

HRID 2250688Notes

Reaction equation

HRID 2250688 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-66b1b1e722e843c09a5e9410d0fed69b
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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