Acetone → HCID 86736728, compound
Reaction equation
[CH3:1][Sn:2]([CH3:10])([CH3:9])[CH2:3][CH2:4][C:5]([NH:7][NH2:8])=[O:6].[CH3:11][C:12]([CH3:14])=O>>[CH3:11][C:12](=[N:8][NH:7][C:5](=[O:6])[CH2:4][CH2:3][Sn:2]([CH3:10])([CH3:9])[CH3:1])[CH3:14]Participants
Procedure
4.0 g (0.016 mole) of 3-trimethylstannylpropionic acid hydrazide of Example 1 and 5.0 ml (0.068 mole) of reagent grade acetone were placed in a 50 ml single-neck flask equipped with a stirrer. The flask was stoppered and the solution was then stirred for about fifteen minutes, at which time the reaction mixture turned solid. Recrystallization of the air-dried solid from acetone-water mixture containing 50% by weight of acetone gave 3.8 g of 3-trimethylstannylpropionic acid 1-methylethylidenehydrazide, Compound 1 of Table I. The infrared spectrum (KBr disc) showed the characteristic bands at 3200 and 3050 cm-1 for N--H and at 1655 and 1550 cm-1 for carbonyl absorption of ##STR9## The carbon-tin bond was characterized by infrared absorption bands at 760, 522, 515 and 503 cm-1. Nuclear magnetic resonance spectroscopy suggested that the compound exists as a tautomeric mixture in CDCl3 solution with one form predominating over the other. The NMR spectra of the dominant isomer showed the following: a broad singlet at 8.38 delta (1H, N--H); a triplet centered at 2.82 delta (2H, --CH2CO); two 3-proton signlets at 1.82 delta and 1.92 delta (--N=C(CH3)2); a triplet centered at 1.02 delta (2H, --CH2Sn); a singlet at 0.06 delta (9H, Sn(CH3)3) flanked by the J(117/119Sn--CH3) doublets.
Workup
- customequipped with a stirrer
- customRecrystallization of the air-dried solid from acetone-water mixture
- additioncontaining 50% by weight of acetone
Sources & evidence
- ORD record
- ord-e7b906748dc6424491961fca7332ab83
- Source dataset
- uspto-grants-1979_12
- Patent number
- US04178382
Reaction notes
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