Benzenesulfonyl chloride → HCID 57624556, compound

HRID 1172876Notes

Reaction equation

HRID 1172876 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:23]=[CH:22][C:13]2[CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:16][C:12]=2[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31]1([S:37](Cl)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([N:8]([CH2:9][C:10]1[CH:23]=[CH:22][C:13]2[CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:16][C:12]=2[CH:11]=1)[S:37]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:39])=[O:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 58968945HCID 58968945, compound

Product 1

HCID 57624556HCID 57624556, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 6-[(benzylamino)methyl]-1-benzothiophene-2-carboxylate (0.147 g, 0.452 mmol) and triethylamine (0.20 mL, 1.43 mmol) in anhydrous CH2Cl2 (1 mL) was slowly added benzene sulphonylchloride (100 μL, 0.784 mmol). The resulting mixture was allowed to stir overnight at room temperature. The solution was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The aqueous layer was washed three times with ethyl acetate. The combined organic layer was dried with sodium sulfate, filtered, and concentrated. The resultant residue was purified by column chromatography yielding the desired product. 1H NMR (CDCl3, 600 MHz) δ 7.97 (d, J=0.6 Hz, 1H), 7.86 (dt, J=8.4, 1.6 Hz, 2H), 7.68 (d, 8.2 Hz, 1H), 7.60 (tt, J=7.2, 1.2 Hz, 1H), 7.51 (t, J=7.2 Hz, 2H), 7.40 (broad s, 1 μl), 7.16-7.19 (m, 3H), 7.09 (dd, J=8.3, 1.5 Hz, 1H), 6.99-7.05 (m, 2H), 4.43 (s, 2H), 4.39 (q, J=7.1 Hz, 2H), 7.35 (s, 2H), 1.40 (t, J=7.1 Hz, 3H). MS: cal'd (MH+), exp 466 (MH+).

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. washThe aqueous layer was washed three times with ethyl acetate
  3. dry with materialThe combined organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-e539875e9e784a8382f3076ed749a691
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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