Chloroacetyl chloride → HCID 19763809, compound

HRID 2166084Notes

Reaction equation

HRID 2166084 reaction equation
O1[CH:7]2[CH:2]1[C:3]([CH3:18])([CH3:17])[O:4][C:5]1[CH:11]=[CH:10][C:9]([CH:12]3CCCC3)=[CH:8][C:6]=12.C([N:21](CC)CC)C.[Cl:26][CH2:27][C:28](Cl)=[O:29]>ClCCl>[Cl:26][CH2:27][C:28]([NH:21][CH:7]1[C:6]2[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:5]=2[O:4][C:3]([CH3:17])([CH3:18])[CH2:2]1)=[O:29]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 14743527HCID 14743527, compound

Product 1

HCID 19763809HCID 19763809, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-3,4-dihydro-2,2,6-dimethyl-2H-1-benzopyran (1.63 g, described in Khim. Geterot. Soed. 5 (3), 434, 1969) in 40 ml dichloromethane at 0° C. was added triethylamine (1.2 ml) followed by chloroacetyl chloride (0.96 g). The solution was stirred for 16 h then washed with saturated brine solution, separated, dried (MgSO4) and concentrated to a cream solid. Chromatography (silica, CH2Cl2 eluent) provided 4-chloroacetamido-3,4-dihydro-2,2,6-trimethyl-2H-1-benzopyran (1.78 g, 78%) as a white solid. m.p. 147°-148° C.

Workup

  1. washthen washed with saturated brine solution
  2. customseparated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to a cream solid

Sources & evidence

ORD record
ord-f965d0bb0a0041b7aef624296aabed78
Source dataset
uspto-grants-1990_07
Patent number
US04943582

Reaction notes

Loading…