Water → HCID 25098363, compound

HRID 39054Notes

Reaction equation

HRID 39054 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:27]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([S:10]([N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=2)[CH3:27])(=[O:12])=[O:11])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25097269HCID 25097269, compound

Product 1

HCID 25098363HCID 25098363, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2′,4′-Dichlorobiphenyl-4-sulfonic acid-(3-hydroxymethyl-phenyl)-amide (ABD455) (0.4 g) was dissolved in DMF (20 ml). K2CO3 (1 g) was added followed by methyl iodide (1 ml). The mixture was stirred vigorously for 3 hrs, poured into water and extracted with ether. After drying (Na2SO4), the solvent was partially removed under vacuum and petrol added to induce crystallisation and the product collected as white crystals. 13C NMR (CDCl3): δ 38.4, 64.7, 125.3, 125.7, 126.0, 127.5, 127.7, 129.2, 129.8, 130.1, 131.9, 133.1, 134.9, 135.8, 137.2, 141.6, 142.0 and 142.8. 1H NMR (CDCl3): δ 3.22 (3H, s), 4.65 (2H, d, J=5.8 Hz), 7.02 (1H, m), 7.14 (1H, s), 7.28 (1H, s), 7.30 (3H, m), 7.48 (2H, d, J=8.2 Hz), 7.50 (1H, m) and 7.60 (2H, d, J=8.2 Hz).

Workup

  1. extractionextracted with ether
  2. dry with materialAfter drying (Na2SO4)
  3. customthe solvent was partially removed under vacuum and petrol
  4. additionadded
  5. customcrystallisation
  6. customthe product collected as white crystals

Sources & evidence

ORD record
ord-9c8f1d4691fc41118313b39a9b3ff803
Source dataset
uspto-grants-2013_09
Patent number
US08524778B2

Reaction notes

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