Carbon Disulfide → HCID 22766682, compound

HRID 866496Notes

Reaction equation

HRID 866496 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH2:8]([CH:10]([CH:15]1[NH:19][CH2:18][CH2:17][O:16]1)[CH2:11][CH2:12][CH2:13][CH3:14])[CH3:9].C(NCC(=CCCCC)O)C.[C:31](=[S:33])=[S:32]>CCOCC>[CH2:8]([CH:10]([CH:15]1[N:19]([C:31]([S-:33])=[S:32])[CH2:18][CH2:17][O:16]1)[CH2:11][CH2:12][CH2:13][CH3:14])[CH3:9].[CH2:1]([NH+:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 2873632-(heptan-3-yl)-1,3-oxazolidineHCID 86735842HCID 86735842, compound

Product 1

HCID 22766682HCID 22766682, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 117 g (1.16 moles) of triethylamine and 133 g (0.77 mole) of 2-(1-ethylpentyl)oxazolidine [containing mainly the tautomer, N-α-ethylpentylidene-2-hydroxyethylamine, and prepared according to A. Cope, J.A.C.S. 64, 1503 (1942)] in 1 liter of ether was added 88 g (1.16 moles) of carbon disulfide at 10°-20° over a period of 35 minutes. Stirring was continued for 17 hours at ambient temperatures. Solids (13 g of triethylammonium N-(2-hydroxyethyl)dithiocarbamate were filtered off and the resulting filtrate was removed of volatiles at 25°/150 mm Hg to give 242g of crude triethylammonium 2-(1-ethylpentyl)-3-oxazolidinecarbodithioate.

Workup

  1. customprepared
  2. filtrationSolids (13 g of triethylammonium N-(2-hydroxyethyl)dithiocarbamate were filtered off
  3. customthe resulting filtrate was removed of volatiles at 25°/150 mm Hg

Sources & evidence

ORD record
ord-15eaa9331c4c4be3a5b5a1f8f98c2350
Source dataset
uspto-grants-1978_07
Patent number
US04099003

Reaction notes

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