Triethylamine → HCID 86739663, compound

HRID 2418700Notes

Reaction equation

HRID 2418700 reaction equation
Cl.[C:2](=[NH:13])([O:9][CH:10]([CH3:12])[CH3:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[S:22][N:23]([CH3:38])[C:24](=[O:37])[O:25][C:26]1[C:34]2[O:33][C:32]([CH3:36])([CH3:35])[CH2:31][C:30]=2[CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[CH3:38][N:23]([C:24]([O:25][C:26]1[C:34]2[O:33][C:32]([CH3:36])([CH3:35])[CH2:31][C:30]=2[CH:29]=[CH:28][CH:27]=1)=[O:37])[S:22][N:13]=[C:2]([O:9][CH:10]([CH3:11])[CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13132231HCID 13132231, compoundHCID 13361608HCID 13361608, compound

Product 1

HCID 86739663HCID 86739663, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of isopropyl benzimidate hydrochloride (18.0 g, 90 mmoles) in methylene chloride (100 ml) at 0° under an atmosphere of dry nitrogen is added a solution of triethylamine (28 ml, 200 mmoles) in a small stream with stirring. To this mixture is added a solution of 2,3-dihydro-2,2-dimethyl-7-benzofuranyl N-chlorothio(methyl)carbamate (26 g, 90 mmoles) in methylene chloride (80 ml) in a dropwise fashion. The reaction mixture is stirred for two hours at 0° and then washed in turn with water, 2N hydrochloric acid and saturated sodium bicarbonate. The organic phase is dried over anhydrous magnesium sulfate and the solvent is removed under reduced pressure. The residue is poured onto a column of silica gel. Elution of the column with a solvent consisting of 15 parts ether and 85 parts Skellysolve B gives from the appropriate fraction isopropyl N-[[methyl[[[2,3-dihydro-2,2-dimethyl-7-benzofuranyl]oxy]carbonyl]amino]thio]benzimidate as a yellow oil.

Workup

  1. stirringThe reaction mixture is stirred for two hours at 0°
  2. washwashed in turn with water, 2N hydrochloric acid and saturated sodium bicarbonate
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. customthe solvent is removed under reduced pressure
  5. additionThe residue is poured onto a column of silica gel
  6. washElution of the column with a solvent

Sources & evidence

ORD record
ord-79675532d1a749839c48bbd084317b24
Source dataset
uspto-grants-1984_09
Patent number
US04473580

Reaction notes

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