Triethylamine → 2-(1-Benzothien-2-yl)-5-[(2-bromobutanoyl)amino]benzamide

HRID 503692Notes

Reaction equation

HRID 503692 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]2[S:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[CH:15]=2)=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].C(N(CC)CC)C.[Br:27][CH:28]([CH2:32][CH3:33])[C:29](Br)=[O:30]>C(Cl)Cl>[S:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[CH:15]=[C:11]1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:29](=[O:30])[CH:28]([Br:27])[CH2:32][CH3:33])=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1172932-Bromobutanoyl bromideHCID 594284755-Amino-2-(1-benzothien-2-yl)benzamide

Product 1

HCID 594284882-(1-Benzothien-2-yl)-5-[(2-bromobutanoyl)amino]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Amino-2-(1-benzothien-2-yl)benzamide (Example 8A, 886 mg) and triethylamine (650 mg) are introduced into DCM (20 ml) at 0° C., and 2-bromobutyryl bromide (1000 mg) is slowly added. The reaction mixture is warmed to RT and then stirred overnight. The reaction mixture is subsequently diluted with DCM (100 ml) and washed with 5% strength potassium bisulfate solution (twice 50 ml), dried (sodium sulfate) and concentrated in a rotary evaporator. The residue is chromatographed on silica gel (eluent cyclohexane-ethyl acetate 10:1 to 1:1). After concentration of the relevant fraction, 607 mg (47% of theory) of product are isolated.

Workup

  1. washwashed with 5% strength potassium bisulfate solution (twice 50 ml)
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in a rotary evaporator
  4. customThe residue is chromatographed on silica gel (eluent cyclohexane-ethyl acetate 10:1 to 1:1)
  5. customAfter concentration of the relevant fraction, 607 mg (47% of theory) of product are isolated

Sources & evidence

ORD record
ord-5de46038a5c34b34aec8ba454fa68e3f
Source dataset
uspto-grants-2010_08
Patent number
US07776922B2

Reaction notes

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