Hydrazine → HCID 12901376, compound

HRID 971697Notes

Reaction equation

HRID 971697 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][Sn:8]([CH3:11])([CH3:10])[CH3:9])=O)C.[NH2:12][NH2:13]>C(O)C>[NH:12]([C:4]([CH2:6][CH2:7][Sn:8]([CH3:11])([CH3:10])[CH3:9])=[O:3])[NH2:13]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 12630295HCID 12630295, compound2×

Product 1

HCID 12901376HCID 12901376, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8 g (30 mmoles) of 2-(ethoxycarbonyl)ethyltrimethylstannane (compound 47), 5 ml of 95% hydrazine (150 mmoles) in 10 ml of ethanol was refuxed for 2 hours. The volatiles were removed at reduced pressure. Distillation of the crude product afforded 5.26 g of 2-(hydrazinocarbonyl)ethyltrimethylstannane, b.p. 92°-98° C. (0.07 mm), compound 42 of Table I. The infrared spectrum of the distillate showed the following characteristic absorptions: 3300 cm-1 (N-H), 1660 cm-1 and 1530 cm-1 ##STR21## and 760 cm-1 (--Sn(CH3)3). A gas chromatogram of the sample showed a single peak on a 6 feet × 1/8 inch commercially obtained column packed with 10% of silicone gum rubber on silanized diatomaceous earth. The NMR spectrum exhibited the following proton absorptions: a broad singlet at 752 Hz (1 proton) assigned to N-H, a singlet at 388 Hz (2 protons) assigned to NH2, a triplet centered at 235 Hz (2 protons) assigned to ##STR22## a triplet centered at 98 Hz (2 protons) assigned to CH2 -Sn, and a singlet centered at 6 Hz (9 protons) assigned to Sn(CH3)3.

Workup

  1. customThe volatiles were removed at reduced pressure
  2. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-fa97120a38ca4c84b505cfcdbc54a478
Source dataset
uspto-grants-1979_07
Patent number
US04160846

Reaction notes

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