Pyridine → HCID 53726966, compound

HRID 614009Notes

Reaction equation

HRID 614009 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[O:9][CH:8]([CH3:10])[CH2:7][C:6]2=[C:11]([NH2:13])[CH:12]=1.N1C=CC=CC=1.[CH2:20]([S:29](Cl)(=[O:31])=[O:30])[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH:13][S:29]([CH2:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])(=[O:31])=[O:30])[C:6]2[CH2:7][CH:8]([CH3:10])[O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1228184423289-99-8HCID 213298112,3-Dihydro-6-methoxy-2-methyl-4-benzofuranamine

Product 1

HCID 53726966HCID 53726966, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 15.5 grams of 2,3-dihydro-6-methoxy-2-methyl-4-benzofuranamine and 10.5 grams of anhydrous pyridine in 100 cc of methylene chloride cooled to 0°-5° C., a solution of 24.5 grams of phenacylsulfonyl chloride in 80 cc of methylene chloride is added. When the dripping is terminated the reaction mixture is warmed to room temperature and stirred for 5 hours. At the end of this time the solution is washed with water, dried over sodium sulfate and concentrated to dryness. Crystallization of the resulting thick oil from ethyl alcohol-ethyl ether gives 16 grams of the compound of the title which melts at 143°-145° C.

Workup

  1. customWhen the dripping is terminated the reaction mixture
  2. washAt the end of this time the solution is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customCrystallization of the resulting thick oil from ethyl alcohol-ethyl ether

Sources & evidence

ORD record
ord-5b737da5db70441ab59ff7293b24faf0
Source dataset
uspto-grants-1979_03
Patent number
US04143055

Reaction notes

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