Triethylamine → HCID 18380104, compound

HRID 2299228Notes

Reaction equation

HRID 2299228 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-b2d0697b2d6640bfbfdbd6ad4544546b
Source dataset
uspto-grants-2002_12
Patent number
US06495643B1

Reaction notes

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