Dichloromethane → HCID 20096923, compound

HRID 1769679Notes

Reaction equation

HRID 1769679 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:8]=1[NH2:9].CN1CCOCC1.[Cl:22]CCl>>[Br:1][CH:2]([Cl:22])[C:3]([NH:9][C:8]1[C:10]([CH3:14])=[CH:11][CH:12]=[CH:13][C:7]=1[CH3:6])=[O:4]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 68962,6-DimethylanilineHCID 79724-MethylmorpholineHCID 89602Bromoacetyl chloride

Product 1

HCID 20096923HCID 20096923, compound

Conditions

Temperature
0 °C

Procedure

A solution of bromoacetyl chloride (20.0 mL, 0.234 mol) in anhydrous dichloromethane (20 mL) was added dropwise to a cold (0° C.) mixture of 2,6-dimethylaniline (29.5 mL, 0.234 mol) and N-methylmorpholine (28.0 mL, 0.254 mol) in anhydrous dichloromethane (500 mL). The mixture was stirred at 0° C. for 1 h and at ambient temperature for 2 h before it was washed with 1N NaOH, 1N HCl and brine. Following drying and solvent evaporation, the residue was triturated with hot ether/ethyl acetate to yield after suction-filtration 46.75 g (83%) of the Formula V compound(s) as an off-white solid, m.p. 148°-149° C.; 1H NMR (300 MHz, CDCl3) δ 8.28 (br s, 1H), 7.08-6.97 (m, 3H), 4.14 (s, 0.5H), 3.93 (s, 1.5H), 2.16 and 2.15 (2s, 6H); 13C NMR (75 MHz, CDCl3) ppm 164.96, 135.63, 133.41, 128.44, 128.39, 127.78, 42.92, 29.04, 18.41; IR (KBr) 3440, 3212, 3042, 2974, 1644, 1534, 1476, 1308, 1218, 1120, 762 cm-1 ; MS (DCI) m/z 242.

Workup

  1. washwas washed with 1N NaOH, 1N HCl and brine
  2. customFollowing drying
  3. customsolvent evaporation
  4. customthe residue was triturated with hot ether/ethyl acetate
  5. customto yield
  6. filtrationafter suction-filtration 46.75 g (83%) of the Formula V compound(s) as an off-white solid, m.p. 148°-149° C.

Sources & evidence

ORD record
ord-1bf4eed855a04367b1c55d30787659cc
Source dataset
uspto-grants-1995_01
Patent number
US05382584

Reaction notes

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