Triethylamine → HCID 86650278, compound

HRID 1889217Notes

Reaction equation

HRID 1889217 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[S:10])=[CH:4][CH:3]=1.[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32](Cl)=[O:33].C(N(CC)CC)C>C(Cl)Cl>[C:19]([C:16]1[CH:15]=[CH:14][C:13]([C:12]([NH:11][C:9](=[S:10])[NH:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:32](=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][Br:24])=[CH:3][CH:4]=2)=[O:23])=[CH:18][CH:17]=1)([CH3:20])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 114022288-bromooctanoyl ChlorideHCID 24772097Tenovin-3

Product 1

HCID 86650278HCID 86650278, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8-Bromooctanoic acid (2 g, 8.90 mmol, 1 equiv) was stirred in CH2Cl2 (15 mL) under N2 atmosphere and thionyl chloride (784 μL, 10.68 mmol, 1.2 equiv) added followed by DMF (few drops). The solution was stirred for 16 h and concentrated in vacuo to give 8-bromooctanoyl chloride (2.04 g, 95%) as a yellow oil which was used without further purification. Thiourea 4 (600 mg, 1.84 mmol, 1 equiv.) was stirred in CH2Cl2 (15 mL) under N2 atmosphere. 8-Bromooctanoyl chloride (532 mg, 2.02 mmol, 1.2 equiv.) was added, followed by triethylamine (256 μL, 1.84 mmol, 1 equiv.). The beige suspension was stirred at rt for 16 h and diluted with CH2Cl2 (20 mL). The organic solution was washed with 1 M aqueous hydrochloric acid (1×20 mL), 10% aqueous sodium hydroxide (1×20 mL), and saturated brine (1×20 mL). The organic phase was dried over MgSO4 and concentrated in vacuo. The resulting yellow foam was purified by flash chromatography on silica (50% ethyl acetate/petroleum ether) to give 8-bromo-octanoic acid {4-[3-(4-tert-butyl-benzoyl)-thioureido]-phenyl}-amide (579 mg, 59%) as a yellow oil.

Workup

  1. customwas used without further purification
  2. washThe organic solution was washed with 1 M aqueous hydrochloric acid (1×20 mL), 10% aqueous sodium hydroxide (1×20 mL), and saturated brine (1×20 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting yellow foam was purified by flash chromatography on silica (50% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-87382f162a6945fcb99165b99644f407
Source dataset
uspto-grants-2013_08
Patent number
US08501991B2

Reaction notes

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