HCID 11663321, compound → HCID 11613229, compound

HRID 2301549Notes

Reaction equation

HRID 2301549 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])=[O:10])=[C:4]([OH:20])[C:3]=1[S:21]([NH:24][CH2:25][CH2:26][CH2:27][S:28][CH3:29])(=[O:23])=[O:22].I([O-])(=O)(=O)=[O:31].[Na+]>C(#N)C.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])=[O:10])=[C:4]([OH:20])[C:3]=1[S:21]([NH:24][CH2:25][CH2:26][CH2:27][S:28]([CH3:29])=[O:31])(=[O:22])=[O:23]

Participants

6

Reactant 2

HCID 11663321HCID 11663321, compoundHCID 23667635Sodium periodate

Product 1

HCID 11613229HCID 11613229, compoundYield 81.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[4chloro-2-hydroxy-3-[N″-(3-methylthiopropyl)aminosulfonyl]-phenyl]-N′-(2,3-dichlorophenyl) urea (50 mg, 0.10 mmol) and sodium periodate (26 mg, 0.12mmol) in acetonitrile (6 mL) and water (2 mL) was stirred for 3 days at room temperature. The mixture was diluted with ethyl acetate and washed with water to give the crude material. Recrystallization from acetone and hexane gave the desired product (42 mg, 81%). 1H NMR (DMSO-d6): δ 9.32 (s, 1H), 9.27 (s, 1H), 8.59 (s, 1H), 8.29 (d, 1H), 8.07 (m, 1H), 7.33 (m, 2H), 7.13 (d, 1H), 3.00 (m, 2H), 2.75 (m, 1H), 2.65 (m, 1H), 2.47 (s, 3H), 1.79 (m, 2H).

Workup

  1. washwashed with water
  2. customto give the crude material
  3. customRecrystallization from acetone and hexane

Sources & evidence

ORD record
ord-24dd8a636eb24cf68a927486e1e4b17a
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

Loading…