Water → HCID 11529749, compound

HRID 1178862Notes

Reaction equation

HRID 1178862 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:20]N(CN(C)C)C.C(OC(=O)C)(=O)C.O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])=[CH2:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5829N,N,N',N'-TetramethylmethanediamineHCID 7918Acetic AnhydrideHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 11529749HCID 11529749, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

2-[[(4-chlorophenyl)sulfonyl]methyl]-1,4-difluorobenzene (Example 2) (100 g, 0.33 mol) and N,N,N′,N′-tetramethyldiaminomethane (34.2 g, 0.50 mol) were dissolved in dimethyl formamide (1000 mL) at 60° C. Acetic anhydride (68.3 g, 1.00 mol) was added slowly and the reaction mixture was aged for 5 hours. Water (1000 mL) was added dropwise and the resulting slurry was cooled to 5° C. The solids were filtered, and the cake washed sequentially with dimethyl formamide:water (40:60, 200 mL) and water (500 mL). Drying overnight in vacuo at 40° C. under a nitrogen stream furnished 2-[1-[(4-chlorophenyl)sulfonyl]ethenyl]-1,4-difluorobenzene (98 g, 95%). 1H NMR (CDCl3) 7.64-7.59 (2H, m), 7.43-7.39 (2H, m), 7.27-7.22 (1H, m), 7.08-6.88 (2H, m), 6.88 (1H, s) and 6.09 (1H, s).

Workup

  1. filtrationThe solids were filtered
  2. washthe cake washed sequentially with dimethyl formamide:water (40:60, 200 mL) and water (500 mL)
  3. customDrying overnight in vacuo at 40° C. under a nitrogen stream

Sources & evidence

ORD record
ord-e5bbdbda8ed94ac49d025f2a187d1d06
Source dataset
uspto-grants-2007_10
Patent number
US07276637B2

Reaction notes

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