Diethylamine → HCID 18519862, compound

HRID 1368065Notes

Reaction equation

HRID 1368065 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:9]=[C:8]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[N:7]([O:19][CH2:20][CH2:21][CH3:22])[CH:6]=1)=[O:4].[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24]>>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([C:8]2[N:7]([O:19][CH2:20][CH2:21][CH3:22])[CH:6]=[C:5]([C:3](=[O:4])[CH2:2][N:25]([CH2:26][CH3:27])[CH2:23][CH3:24])[CH:9]=2)=[O:18])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 18519856HCID 18519856, compound

Product 1

HCID 18519862HCID 18519862, compoundYield 26%

Procedure

A solution of 3.19 g (0.0094 mole) of 2-chloro-1-[5-(4-chlorobenzoyl)-1-ethylmethoxy-1H-pyrrol-3-yl]ethanone, 75 mL of 2-PrOH, and 2.9 mL (0.028 mole) of diethylamine was heated under reflux for 4 h. The solvent was evaporated in vacuo. The residue was partitioned between Et2O and 2N NaOH. The organics were washed with water, brine and dried (Na2SO4). The solvent was evaporated in vacuo and the residue chromatographed on silica gel (9:1 CH2Cl2: MeOH). The oil was treated with ethereal HCl and the resulting solid recrystallized from 2-PrOH to give 0.9 g (26%) of Compound 9. mp 149-151° C. CIMS m/z 377 (MH+). 1H NMR (300 MHz, DMSO-d6) δ 8.2 (Ar, 1H); 7.8 (Ar, 2H); 7.7 (Ar, 2H); 7.2 (Ar, 1H); 4.7 (m, 2H); 4.6 (t, 2H); 3.65 (t, 2H); 3.2 (m, 3H); 3.15 (m, 4H); 1.2 (t, 6H). Calc'd for: C20H25CIN2O3.HCl: C, 5.12; H, 634; N, 6.78. Found: C, 58.29; H, 6.31; N, 6.55.

Workup

  1. temperatureunder reflux for 4 h
  2. customThe solvent was evaporated in vacuo
  3. customThe residue was partitioned between Et2O and 2N NaOH
  4. washThe organics were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated in vacuo
  7. customthe residue chromatographed on silica gel (9:1 CH2Cl2: MeOH)
  8. additionThe oil was treated with ethereal HCl
  9. customthe resulting solid recrystallized from 2-PrOH

Sources & evidence

ORD record
ord-efcc11602b504eb5b45f363e68c2c4ba
Source dataset
uspto-grants-2003_06
Patent number
US06573267B2

Reaction notes

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