Nitrogen → HCID 13309741, compound

HRID 1903891Notes

Reaction equation

HRID 1903891 reaction equation
N#N.C(Cl)(Cl)(Cl)Cl.C(=O)=O.[CH2:11]=[C:12]([CH2:18][CH3:19])[CH2:13][CH2:14][CH:15]([OH:17])[CH3:16].ClN1C(=O)CCC1=O.CSC>C1(C)C=CC=CC=1.CCOCC.C(N(CC)CC)C>[CH2:11]=[C:12]([CH2:18][CH3:19])[CH2:13][CH2:14][C:15](=[O:17])[CH3:16]

Participants

9

Reactant 5

HCID 947NitrogenHCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 13309742HCID 13309742, compoundHCID 86602444Carbontetrachloride dry-ice

Product 1

HCID 13309741HCID 13309741, compoundYield 36.2%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

With exclusion of moisture (N2) and cooling (-19° C., carbon tetrachloride-dry ice slush bath), a solution of 19.23 g 5-methylene-2-heptanol in toluene was added to a stirred mixture of 30.04 g N-chlorosuccinimide and 19.10 g dimethyl sulfide in toluene. The mixture was allowed to warm to ca 25° C. over a two-hour period. Then 23.2 g triethylamine was added. After five minutes, the reaction mixture was diluted two-fold with ether. Upon washing with 1% hydrochloric acid and then water, the organic phase was dried (magnesium sulfate) and concentrated. Distillation afforded 6.85 g product with bp 73°-76° C. (20 torr).

Workup

  1. temperatureto warm to ca 25° C. over a two-hour period
  2. washUpon washing with 1% hydrochloric acid
  3. dry with materialwater, the organic phase was dried (magnesium sulfate)
  4. concentrationconcentrated
  5. distillationDistillation

Sources & evidence

ORD record
ord-f227b338c9384fd48eea631f5bc541e2
Source dataset
uspto-grants-1984_03
Patent number
US04439225

Reaction notes

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