Benzenesulfonyl chloride, 2,4-dichloro- → HCID 59864816, compound

HRID 2423301Notes

Reaction equation

HRID 2423301 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:15][C:14]=1[Cl:24].[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1>[Cl:24][C:14]1[CH:15]=[C:16]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:18][C:13]=1[O:12][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([S:33]([C:27]3[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:26]=3[Cl:25])(=[O:35])=[O:34])[C:8]([CH3:11])=[N:9][C:10]=2[C:2]=1[NH:1][S:33]([C:27]1[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:26]=1[Cl:25])(=[O:35])=[O:34]

Participants

4

Reactant 2

HCID 204419Benzenesulfonyl chloride, 2,4-dichloro-HCID 59864908HCID 59864908, compound

Product 1

HCID 59864816HCID 59864816, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under an N2 atmosphere, methyl 2-(4-(4-amino-2-methyl-1H-benzo[d]imidazol-5-yloxy)-3-chlorophenyl)acetate (0.171 g, 0.495 mmol) was dissolved in pyridine (1.5 mL) and 2,4-dichlorobenzenesulfonyl chloride (0.267 g, 1.09 mmol) was added. The reaction was allowed to stir at room temperature for 3 h and then concentrated in vacuo. Flash column chromatography of the residue, eluting 0% to 50% ethyl acetate in hexanes, afforded the title compound. LC-MS ESI (pos.) m/z: 763.7 (M+H).

Workup

  1. concentrationconcentrated in vacuo
  2. washFlash column chromatography of the residue, eluting 0% to 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f840e7960f584b099efb32d9eb963f7d
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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