Acetone → HCID 13067815, compound

HRID 358532Notes

Reaction equation

HRID 358532 reaction equation
C[O-].[Na+].[SH2:4].Br[CH:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:7]=O.[CH3:14][C:15]([CH3:17])=O.[NH3:18]>O.CO>[CH3:14][C:15]1([CH3:17])[N:18]=[CH:7][CH:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[S:4]1

Participants

8

Reactant 5

HCID 180AcetoneHCID 222AmmoniaHCID 402Hydrogen SulfideHCID 109103842-bromoheptanalHCID 10942334Sodium Methoxide

Product 1

HCID 13067815HCID 13067815, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

The procedure of M. Thiel, F. Asinger, K. Schmiedel, (Liebigs Ann. Chem. 611, 121 (1958)) was employed. To a methanol solution (3 liters) containing sodium methoxide (216.7 g, 4.01 mole) at -10° C. was added hydrogen sulfide (~1 lb) until the solution was saturated. To this solution was added dropwise over a 2 hour period 2-bromoheptaldehyde (775 g, 4.01 mol). The temperature of the reaction was maintained at about -10° C. after the addition, acetone (734 g, 12.6 mole) was added over a 10 minute period and the solution was stirred for an additional 20 minutes at about -10° C. at which time ammonia was added over a period of 1.5 hours. The solution was then poured into water (4 liters) and extracted with ether (4×1 liter). The combined etheral extracts were washed with brine (1×1 liter), dried over magnesium suflate and concentrated in vacuo to afford after distillation (70°-80°/1.5 mm) 549 g (74%) of 2,2-dimethyl-5-pentyl-3-thiazoline. ;NMR (d, CDCl3) 0.6-2.2 (11H, m, CH2,CH3) 1.70 (6H, s, C(CH3)2), 4.3-4.65 (1H, m, CHS), 7.10 (1H, d, CHN).

Workup

  1. additionwas added over a 10 minute period
  2. additionwas added over a period of 1.5 hours
  3. extractionextracted with ether (4×1 liter)
  4. washThe combined etheral extracts were washed with brine (1×1 liter)
  5. dry with materialdried over magnesium suflate
  6. concentrationconcentrated in vacuo
  7. customto afford
  8. distillationafter distillation (70°-80°/1.5 mm) 549 g (74%) of 2,2-dimethyl-5-pentyl-3-thiazoline

Sources & evidence

ORD record
ord-32b061a4caff49ea91745e750d618f98
Source dataset
uspto-grants-1984_08
Patent number
US04468516

Reaction notes

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