Allylamine → 6-Chloro-3,4-dihydro-N-2-propen-1-yl-2H-1-benzopyran-2-carboxamide

HRID 1447785Notes

Reaction equation

HRID 1447785 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([OH:13])=O)[CH2:8][CH2:7][C:6]=2[CH:14]=1.[CH2:15]([NH2:18])[CH:16]=[CH2:17]>S(Cl)(Cl)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:11]([NH:18][CH2:15][CH:16]=[CH2:17])=[O:13])[CH2:8][CH2:7][C:6]=2[CH:14]=1

Participants

5

Reactant 2

HCID 7853AllylamineHCID 232739172H-1-BENZOPYRAN-2-CARBOXYLIC ACID, 6-CHLORO-2,3-

Product 1

HCID 203830626-Chloro-3,4-dihydro-N-2-propen-1-yl-2H-1-benzopyran-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent2×

Procedure

A solution of 3.1 g of 6-chloro-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid (1A) (Witiak et al. (1971), supra) in 15 ml of thionyl chloride was refluxed for 45 minutes. The excess thionyl chloride then was stripped off and the residual liquid taken up in 50 ml of methylene chloride. To this stirred solution was added dropwise a solution of 2.5 g of 2-propenamine in 10 ml of methylene chloride. The resulting mixture was stirred at room temperature overnight, then was washed with water, dried (MgSO4) and stripped of solvent. Dry column chromatography of the solid product through silica gel, using Solvent No. 3 (a 4:30:66 by volume mixture of tetrahydrofuran, ethyl acetate and hexane) as eluent, followed by recrystallization of the product from ethylene chloride and hexane gave 1, as a pale yellow solid, mp: 112.5°-114° C. Example 2

Workup

  1. washwas washed with water
  2. dry with materialdried (MgSO4)
  3. customDry column chromatography of the solid product through silica gel
  4. addition3 (a 4:30:66 by volume mixture of tetrahydrofuran, ethyl acetate and hexane) as eluent
  5. customfollowed by recrystallization of the product from ethylene chloride and hexane
  6. customgave 1

Sources & evidence

ORD record
ord-6cdce16417be4ddf8e00f030d1aa3cdb
Source dataset
uspto-grants-1979_12
Patent number
US04178380

Reaction notes

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