Tributyltin Chloride → HCID 85779503, compound

HRID 1288361Notes

Reaction equation

HRID 1288361 reaction equation
[CH3:1][N:2]([S:4]([CH2:7][Li])(=[O:6])=[O:5])[CH3:3].[CH2:9]([Sn:13](Cl)([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12].[Cl-].[NH4+]>CCCCCC.C1COCC1.C1COCC1>[CH3:1][N:2]([S:4]([CH2:7][Sn:13]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:9][CH2:10][CH2:11][CH3:12])(=[O:6])=[O:5])[CH3:3]

Participants

6

Reactant 3

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 178506888HCID 178506888, compound

Product 1

HCID 85779503HCID 85779503, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21883165Tetrahydrofuran hexaneSolvent

Conditions

Temperature
20 °C

Procedure

Employing the apparatus and procedure of Example I, 100 ml. of an approximately one-molar solution of (N,N-dimethylaminosulfonylmethyl)lithium in hexane-THF solvent was added slowly over a period of 30 minutes to 0.1 mole of tri-n-butyltin chloride dissolved in THF. The temperature at addition was -60° C provided by a dry ice-acetone bath and rose through the addition period to 0° C. Following the complete addition, the reaction mixture was stirred for 2 hours at room temperature (20° C) and hydrolyzed by pouring into an aqueous one-molar ammonium chloride solution. Extraction from the hydrolyzate with ether solvent and purification by vacuum distillation yielded the desired compound, (N,N-dimethylaminosulfonylmethyl)tributyltin. The product, a pale-yellow liquid, had a boiling point of from 158°-160° C/0.1 mm. Hg. Analysis gave 43.8% Carbon and 8.5% Hydrogen compared to the calculated values, respectively, of 43.7% and 8.5%. The assigned structure was confirmed by infrared and proton nuclear magnetic resonance spectral analyses.

Workup

  1. additionThe temperature at addition
  2. customwas -60° C
  3. customprovided by a dry ice-acetone bath
  4. additionrose through the addition period to 0° C
  5. additionthe complete addition
  6. extractionExtraction from the hydrolyzate
  7. customwith ether solvent and purification
  8. distillationby vacuum distillation

Sources & evidence

ORD record
ord-994cb39c1c194cccb7ce7296b16049d7
Source dataset
uspto-grants-1976_10
Patent number
US03988145

Reaction notes

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