Chloroacetyl chloride → HCID 899189, compound

HRID 2283208Notes

Reaction equation

HRID 2283208 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].Cl[CH2:12][C:13](Cl)=[O:14].[CH2:16]([NH:18][CH2:19][CH3:20])[CH3:17]>C1COCC1>[CH2:16]([N:18]([CH2:19][CH3:20])[CH2:12][C:13]([NH:7][C:6]1[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:14])[CH3:17]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 74233-NitroanilineHCID 8021Diethylamine

Product 1

HCID 899189HCID 899189, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-nitroaniline (1.00 g, 7.24 mmol) in THF (20 ml) was cooled to 4° C. in an ice bath. To this stirred mixture TEA (1.47 g, 14.50 mmol), then chloroacetyl chloride (0.98 g, 8.70 mmol) were sequentially added. The reaction was allowed to warm up to room temperature and after 2 and a half hours diethylamine (1.59 g, 21.7 mmol) was added in ice bath and the resulting mixture stirred overnight at room temperature. After completion (TLC 5% MeOH in DCM), solvent was evaporated in vacuo. The crude product was dissolved in DCM (75 ml), washed 3 times with saturated aqueous NaHCO3 solution (50 ml), dried (MgSO4), filtered and taken to dryness in vacuo. The crude product thus obtained was purified by flash column chromatography (0%-5% MeOH in DCM) to give 2-(diethylamino)-N-(3-nitrophenyl)acetamide 4 as a yellow semi-solid (0.92 g, 50%); Rf 0.26 [5% MeOH in DCM]; δH (CDCl3, 400 MHz) 9.68 (1H, s, NH), 8.36-8.35 (1H, m, ArH), 8.05-8.03 (1H, m, ArH), 7.93 (1H, dd, J1=8.4 Hz, J2=1.6 Hz, ArH), 7.51.7.57 (1H, m, ArH), 3.18 (2H, s, CH2), 2.67 (4H, quartet, J=7.2 Hz, 2×CH2), 1.10 (6H, t, J=7.2 Hz, 2×CH3); δC (CDCl3, 100 MHz) 169.95 (C═O), 147.27 (Ar—C), 138.64 (Ar—C), 129.61 (Ar—CH), 110.74 (Ar—CH), 109.17 (Ar—CH), 105.92 (Ar—CH), 58.14 (CH2), 48.79 (2×CH2), 12.39 (2×CH3); LC-MS (5 min) m/z 252.37 [C12H17N3O3+H]+ (100), Rt 0.83 min; HRMS m/z calc C12H18N3O3 [M+H]+252.1353. found [M+H]+252.1358; anal. CHN calc. C12H17N3O3. C, 57.4%; H, 6.8%; N, 16.7%. found C, 57.3%; H, 7.1%; N, 16.6%.

Workup

  1. customAfter completion (TLC 5% MeOH in DCM), solvent was evaporated in vacuo
  2. dissolutionThe crude product was dissolved in DCM (75 ml)
  3. washwashed 3 times with saturated aqueous NaHCO3 solution (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe crude product thus obtained
  7. customwas purified by flash column chromatography (0%-5% MeOH in DCM)

Sources & evidence

ORD record
ord-616769d3e6424a57b768b1ff0aeb6598
Source dataset
uspto-grants-2015_09
Patent number
US09145377B2

Reaction notes

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