Triethylamine → HCID 18380104, compound

HRID 1638131Notes

Reaction equation

HRID 1638131 reaction equation
Cl[C:2]([Cl:12])(OC(=O)OC(Cl)(Cl)Cl)Cl.OC[CH:15]1[CH2:21][S:20][CH2:19][C:18](=[CH2:22])[CH2:17][S:16]1.C(N(CC)CC)C>ClCCl>[Cl:12][CH2:2][CH:15]1[CH2:21][S:20][CH2:19][C:18](=[CH2:22])[CH2:17][S:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429Triphosgene3×HCID 22670481HCID 22670481, compound

Product 1

HCID 18380104HCID 18380104, compoundYield 198.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triphosgene (0.843 g, 2.84 mmoles) was dissolved in 20 mL of dichloromethane. 2-(Hydroxymethyl)-6-methylene-1,4-dithiepane (1.5 g, 8.52 mmoles) and triethyl amine (1.185 mL, 0.86 g) were dissolved in ca. 5 mL of dichloromethane and added dropwise to the triphosgene solution. After ca. one hour the reaction was largely complete. A little more triphosgene was added and the solution was stirred overnight. The reaction was worked up by evaporation of solvent, addition of water and extraction with ether. The extracts were dried and evaporated and the resulting oil was chromatographed on silica gel to give 1.1 g (67%) of clear oil.

Workup

  1. customThe reaction was worked up by evaporation of solvent, addition of water and extraction with ether
  2. customThe extracts were dried
  3. customevaporated
  4. customthe resulting oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-fe9e342c92bb49adb31cdfc85f4d8269
Source dataset
uspto-grants-2000_03
Patent number
US06043361

Reaction notes

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