Dimethylformamide → HCID 43091056, compound

HRID 1801555Notes

Reaction equation

HRID 1801555 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:15]=[CH:14][C:9]2[O:10][CH2:11][CH2:12][O:13][C:8]=2[CH:7]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:22][O:23][CH2:24][CH2:25][NH2:26].CN(C=O)C>O>[O:10]1[C:9]2[CH:14]=[CH:15][C:6]([NH:5][C:3](=[O:4])[CH2:2][NH:26][CH2:25][CH2:24][O:23][CH3:22])=[CH:7][C:8]=2[O:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80182-MethoxyethylamineHCID 11430Potassium CarbonateHCID 31521162-chloro-N-(2,3-dihydro-1,4-benzodioxin-6-yl)acetamide

Product 1

HCID 43091056HCID 43091056, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-N-(2,3-dihydro-1,4-benzodioxin-6-yl)acetamide (2 mmol), potassium carbonate (10 mmol), 2-methoxyethylamine (2 mmol) and anhydrous DMF (4 mL) was stirred for 2 hours at 100° C. (monitored by TLC). The mixture was cooled to room temperature, treated with cold water (30 mL). The precipitate was collected by filtration, washed with diethyl ether and dried to afford N-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2-(2-methoxy-ethylamino)-acetamide (Compound XIa, 96 mg, 36%). 1H NMR (300 MHz, CDCl3/TMS): δ=9.29 (s, 1H), 7.24 (d, 1H, J=2.4 Hz), 6.97 (dd, 1H, J=8.7, 2.4 Hz), 6.78 (d, 1H, J=8.7 Hz), 4.32-4.15 (m, 4H), 3.46 (t, 2H, 4.8 Hz), 3.36 (s, 3H), 3.34 (s, 2H), 2.82 (t, 2H, J=4.8 Hz), 2.17 (s, 1H). 13C NMR (75 MHz, CDCl3/CD3OD/TMS): δ=169.48, 143.16, 139.87, 131.43, 116.84, 112.74, 108.89, 71.41, 64.28, 64.12, 58.68, 52.57, 49.35.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-2db42a74ad1447bc9d66f1b0f78100ea
Source dataset
uspto-grants-2013_01
Patent number
US08349833B2

Reaction notes

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