Triethylamine → (2,3-Dihydro-6-methoxy-2-methyl-4-benzofuranyl)carbamic acid ethyl ester

HRID 614003Notes

Reaction equation

HRID 614003 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[O:15][CH:14]([CH3:16])[CH2:13][C:12]2=[C:17]([NH2:19])[CH:18]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:5])[NH:19][C:17]1[C:12]2[CH2:13][CH:14]([CH3:16])[O:15][C:11]=2[CH:10]=[C:9]([O:8][CH3:7])[CH:18]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 213298112,3-Dihydro-6-methoxy-2-methyl-4-benzofuranamine

Product 1

HCID 54490261(2,3-Dihydro-6-methoxy-2-methyl-4-benzofuranyl)carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

55.75 grams of ethylchlorocarbonate in 100 cc of anhydrous benzene are gradually added at 5° C. to a stirred solution of 81 grams of 2,3-dihydro-6-methoxy-2-methyl-4-benzofuranamine and 46 cc of triethylamine in 700 cc of anhydrous benzene. At the end of the addition, the reaction mixture is slightly warmed and stirring is continued, at room temperature, for 3 hours. After this time the reaction mixture is refluxed for two hours, then cooled, washed with water, dried over Na2SO4 and concentrated to dryness yielding 95.81 grams (83.5 percent of theoretical) of the compound of the title B.p./0.4 mmHg 172° C.

Workup

  1. additionAt the end of the addition
  2. temperaturethe reaction mixture is slightly warmed
  3. temperatureAfter this time the reaction mixture is refluxed for two hours
  4. temperaturecooled
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customyielding 95.81 grams (83.5 percent of theoretical) of the compound of the title B.p
  9. custom0.4 mmHg 172° C.

Sources & evidence

ORD record
ord-f71a2f5db6e1448f8ae66d1e315a01b0
Source dataset
uspto-grants-1979_03
Patent number
US04143055

Reaction notes

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