Triethylamine → HCID 90411149, compound

HRID 2170839Notes

Reaction equation

HRID 2170839 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[NH2:7].C(N(CC)CC)C.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>C1COCC1>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:7][N:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:28])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 12362512HCID 12362512, compound

Product 1

HCID 90411149HCID 90411149, compoundYield 77,087.797%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 1-(thiophen-2-yl)hydrazinecarboxylate (100 mg, 0.467 mmol) in THF (5 mL) was added triethylamine (64 μL, 0.476 mmol, 1 eq.) and 4-chlorobenzoyl chloride (60 μL, 82 mg, 0.467 mmol, 1 eq.), and the resulting mixture was stirred for 1 hour at room temperature. A sample of the reaction mixture (quenched in water, and extracted with EtOAc) showed the presence of the intermediate crude product tert-butyl 2-(4-chlorobenzoyl)-1-(thiophen-2-yl)-hydrazinecarboxylate, as determined by NMR. The reaction mixture was then poured in water and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated in vacuo. The crude product (278 mg) was purified by automated column chromatography (EtOAc/heptane) to yield tert-butyl 2-(4-chlorobenzoyl)-1-(thiophen-2-yl)-hydrazinecarboxylate (127 mg, 360 mmol, yield 77%) as a light brown solid with an HPLC purity of greater than 99%. LC-MS (M−1) 351 (C16H17ClN2O3S-1, expected 352.06).

Workup

  1. customA sample of the reaction mixture (quenched in water, and extracted with EtOAc)
  2. additionThe reaction mixture was then poured in water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product (278 mg) was purified by automated column chromatography (EtOAc/heptane)

Sources & evidence

ORD record
ord-e719c5e918524db09d9bbb71dfc071c4
Source dataset
uspto-grants-2015_06
Patent number
US09051309B2

Reaction notes

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