Water → HCID 59392453, compound

HRID 570862Notes

Reaction equation

HRID 570862 reaction equation
[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]([OH:6])=[C:3]1[OH:4].[C:13]1([C:19]2[NH:20][C:21]3[CH:27]=[C:26]([S:28](Cl)(=[O:30])=[O:29])[CH:25]=[CH:24][C:22]=3[N:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.C(Cl)(Cl)Cl>CN(C=O)C.CN(C)C1C=CN=CC=1>[C:13]1([C:19]2[NH:20][C:21]3[CH:27]=[C:26]([S:28]([O:12][CH2:11][C@H:9]([C@@H:7]4[C:5]([OH:6])=[C:3]([OH:4])[C:2](=[O:1])[O:8]4)[OH:10])(=[O:29])=[O:30])[CH:25]=[CH:24][C:22]=3[N:23]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 195939542-Phenyl-1H-benzimidazole-6-sulfonyl chlorideHCID 54670067L-Ascorbic Acid

Product 1

HCID 59392453HCID 59392453, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

45.1 g of ascorbic acid (255.2 mmol; 3 eq.) are dissolved in 100 ml of DMF, 521 mg of 4-dimethylaminopyridine (4.27 mmol; 0.05 eq.) are added, and 25 g of 2-phenyl-3H-benzimidazole-5-sulfonyl chloride (85.4 mmol; 1 eq.), dissolved in 66 ml of DMF, are added dropwise at 0° C. The mixture is subsequently warmed to room temperature, and, after 6 hrs., 100 ml of water and 100 ml of chloroform are added, the mixture is extracted, dried, and the solvent is removed in vacuo. The residue is recrystallised from toluene, giving the product as a pale-beige solid.

Workup

  1. additionare added dropwise at 0° C
  2. extractionthe mixture is extracted
  3. customdried
  4. customthe solvent is removed in vacuo
  5. customThe residue is recrystallised from toluene

Sources & evidence

ORD record
ord-7e3c08f21b934af2b618d232b09cbb4e
Source dataset
uspto-grants-2015_05
Patent number
US09023889B2

Reaction notes

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