2,5-Dichloroaniline → HCID 178512050, compound

HRID 1466406Notes

Reaction equation

HRID 1466406 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH2:4].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Br:20][C:21]1[S:25][C:24]([C:26]#[N:27])=[CH:23][CH:22]=1>C1COCC1>[Br:20][C:21]1[S:25][C:24]([C:26]([NH:4][C:3]2[CH:5]=[C:6]([Cl:9])[CH:7]=[CH:8][C:2]=2[Cl:1])=[NH:27])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 72622,5-DichloroanilineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 35950595-Bromothiophene-2-carbonitrile

Product 1

HCID 178512050HCID 178512050, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under N2 atmosphere, to a solution of 2,5-dichloroaniline (341 mg, 2.1 mmol) in 2 mL dry THF was added sodium bis(trimethylsilyl)amide (2.1 mL, 1M solution in THF, 2.1 mmol). After the mixture was stirred at ambient temperature for 40 min, a solution of 5-bromo-thiophene-2-carbonitrile (376 mg, 2 mmol) in 2 mL dry THF was added dropwise. The reaction mixture was stirred overnight, and then poured into 100 mL ice water. The orange precipitate was collected by filtration, washed with a solution of ether and hexane (3/7, v/v), and air dried to give a light orange solid (653 mg, 94% yield). 1H-NMR (400 MHz, MeOH-d4): δ 6.94 (d, 1H), 6.99 (dd, 1H), 7.06 (d, 1H), 7.32 (d, 1H), 7.37 (d, 1H).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. filtrationThe orange precipitate was collected by filtration
  3. washwashed with a solution of ether and hexane (3/7
  4. customv/v), and air dried

Sources & evidence

ORD record
ord-0910f2f0938e4f3d9d3839a526865cdc
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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