Benzenepropanoyl chloride → HCID 2852196, compound

HRID 537327Notes

Reaction equation

HRID 537327 reaction equation
[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)[CH3:2].CCN(C(C)C)C(C)C.[C:23]1([CH2:29][CH2:30][C:31](Cl)=[O:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:31](=[O:32])[CH2:30][CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 64801Benzenepropanoyl chloride2×HCID 692294-Ethoxy-2-nitroanilineHCID 81531Diisopropylethylamine

Product 1

HCID 2852196HCID 2852196, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A 500 mL 3-neck flask fitted with a stir-bar, addition funnel, and an Ar inlet was charged with aniline 46a (4.00 g, 22.0 mmol) and CH2Cl2 (80 mL). To the resultant solution was added iPr2NEt (7.10 g, 55.0 mmol) followed by acid chloride 74 (4.27 g, 25.3 mmol) in CH2Cl2 (40 mL) over 15 min. The mixture stirred at rt overnight. Another 0.75 g of acid chloride 74 was added, and the mixture stirred 2 hr to completion as monitored by HPLC. The solution was diluted with CH2Cl2 (100 mL) and washed with saturated aqueous NaHCO3 (125 mL) and brine (100 mL). The solution was filtered through phase separation paper and concentrated in vacuo to an oil/solid mix. The solid was collected with hexanes:EtOAc 4:1 (30 mL) and rinsed with hexanes:EtOAc 4:1 (2×10 mL). The material was dried to give 4.85 g of 75 as an orange solid (70%). 1H NMR (60 MHz, CDCl3): δ 9.8 (bs, 1H), 8.8 (d, 1H), 7.9 (d, 1H), 7.6 (s, 5H), 7.4 (d, 1H), 4.2 (qt, 2H), 3.1 (m, 4H), 1.5 (t, 3H) ppm. HPLC analysis (15:10:75 H2O:A1:MeOH) showed a purity of 98% with a retention time of 6.9 min.

Workup

  1. customA 500 mL 3-neck flask fitted with a stir-bar, addition funnel
  2. stirringthe mixture stirred 2 hr to completion
  3. washwashed with saturated aqueous NaHCO3 (125 mL) and brine (100 mL)
  4. filtrationThe solution was filtered through phase separation paper
  5. concentrationconcentrated in vacuo to an oil/solid
  6. additionmix
  7. customThe solid was collected with hexanes:EtOAc 4:1 (30 mL)
  8. washrinsed with hexanes:EtOAc 4:1 (2×10 mL)
  9. customThe material was dried

Sources & evidence

ORD record
ord-d7d72f55b805484892908407126efa3f
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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