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Tributyltin Chloride → HCID 22609752, compound

HRID 1936774
Notes
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Reaction equation

HRID 1936774 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1)[CH3:3].[Li]CCCC.[CH2:17]([Sn:21](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>C1COCC1>[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 178703301H-Imidazole-1-propanamine, N,N-dimethyl-HCID 178418339Butyllithium

Product 1

HCID 22609752HCID 22609752, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

1-(N,N-Dimethylaminopropyl)imidazole (2 g) in THF (20 ml) at −78° C. was treated with nBuLi (8.6 ml, 1.6M) under nitrogen. After 30 minutes at −78° C., tri-n-butylstannyl chloride was added and the mixture allowed to warm to 20° C. The mixture was concentrated in vacuo, taken up in n-hexane and filtered. The filtrate was concentrated in vacuo to give the title compound (4.33 g) as a yellow oil; δH CDCl3 7.28 (1H,s), 7.09 (1H,s), 3.97 (2H,t), 2.25 (2H,t), 2.20 (6H,s), 1.90 (2H,m) 1.55 (6H,m), 1.34 (12H,m), 0.92 (9H,m).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-25e2bbf414b142569a31daf0ae4e65ec
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06391874B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes