2-Amino-5-(methanesulfonyl)benzoic acid → 4-(methylsulfonyl)-Biphenyl-2-carboxylic acid

HRID 2117458Notes

Reaction equation

N[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N([O-])=O.[Na+]>S(=O)(=O)(O)O.O>[CH3:14][S:11]([C:8]1[CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]([C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:3]=2)=[CH:10][CH:9]=1)(=[O:13])=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 3.0 mmol 2-amino-5-methanesulfonyl-benzoic acid in a mixture of 1.7 ml sulfuric acid and 1.7 ml water was added dropwise a solution of 3.92 mmol sodium nitrite in 1.7 ml water at such rate that the temperature did not exceed 3° C. The mixture was stirred at 0° C. for 1 hour. A solution of 3.0 mmol KI in 1.7 ml water was added dropwise at 0° C. The brown suspension was allowed to warm to rt and stirred for 30 minutes. Excess iodine was destroyed by addition of a few drops of a sodium hydrogenosulfite solution. The solid was filtered, washed with water and dried (HV, 50° C., 1 hour) to yield the title compound. MS (m/e): 325.0 (M−H, 100%)

Workup

customdid not exceed 3° C
temperatureto warm to rt
stirringstirred for 30 minutes
customExcess iodine was destroyed by addition of a few drops of a sodium hydrogenosulfite solution
filtrationThe solid was filtered
washwashed with water
customdried (HV, 50° C., 1 hour)

Sources & evidence

ORD record: ord-775d6149a5d646a3b8e8fe8ee1bbf2cb
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442710B2

Reaction notes

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