Water → HCID 14995292, compound

HRID 2248906Notes

Reaction equation

HRID 2248906 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:31]=[CH:32][CH:33]=1)[CH2:16][O:17][C:18]1[CH:30]=[CH:29][C:21]2[S:22][C:23]([C:26]([NH2:28])=O)=[C:24]([CH3:25])[C:20]=2[CH:19]=1.CS(Cl)(=O)=O.O.C(OCC)(=O)C>N1C=CC=CC=1>[C:26]([C:23]1[S:22][C:21]2[CH:29]=[CH:30][C:18]([O:17][CH2:16][C:15]3[CH:31]=[CH:32][CH:33]=[C:13]([O:12][CH2:11][C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=4)[CH:14]=3)=[CH:19][C:20]=2[C:24]=1[CH3:25])#[N:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 14995291HCID 14995291, compound

Product 1

HCID 14995292HCID 14995292, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 5-[3-(2-quinolinylmethyloxy)benzyloxy]-3-methylbenzo(b)thiophene-2-carboxamide (454.5 mg, 1 mmol) in pyridine (10 ml) at room temperature is added methanesulfonyl chloride (387 μL, 5 mmol). The solution is stirred for 16 hours and water (50 ml) and ethyl acetate (100 ml) are added. Extraction with ethyl acetate, washing with water and brine, drying (MgSO4) and concentration affords a crude product which is chromatographed over silica gel. Elution with 25% ethyl acetate in hexane provides 2-cyano-5-[3-(2-quinolinylmethyloxy)benzyloxy]-3-methylbenzo(b)thiophene.

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with water and brine
  3. customdrying
  4. concentration(MgSO4) and concentration
  5. customaffords a crude product which
  6. customis chromatographed over silica gel
  7. washElution with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-15df2946e4f24be0a1c695c7d871328b
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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