Water → HCID 86591957, compound

HRID 2103739Notes

Reaction equation

HRID 2103739 reaction equation
[C:1]([O:5][C:6]([CH2:8][NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19](C1NC=CN=1)([C:21]1[NH:22][CH:23]=[CH:24]N=1)=O.C(NCC)C.O>O1CCCC1>[CH2:21]([N:22]([CH2:23][CH3:24])[C:13](=[O:15])[C:12]1[CH:16]=[CH:17][CH:18]=[C:10]([NH:9][CH2:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:11]=1)[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 69063794HCID 69063794, compound

Product 1

HCID 86591957HCID 86591957, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(N-tert-butoxycarbonylmethylamino)benzoic acid (10.0 g, 39.8 mmol) in 100 mL of tetrahydrofuran was added carbonyl diimidazole (6.78 g, 41.8 mmol) under Argon. After 2 h of stirring, diethylamine (5.82 g, 79.4 mmol) was added, and the reaction mixture was stirred for 18 h and then refluxed 3 h. After cooling, water (50 mL) was added to the reaction flask, and the contents were concentrated on a rotary evaporator. The resulting mixture was extracted three times with dichloromethane (50 mL). These extracts were combined, washed twice with 1 N aqueous hydrochloric acid solution (50 mL) and twice with water (50 mL), dried (Na2SO4), and concentrated to give 11.9 g (98%) of N,N-diethyl 3-(N-tert-butoxycarbonylmethylamino)benzamide as a yellow oil. MS (ES), m/z 307 (MH+). 300 MHz 1H NMR (CDCl3) δ1.03-1.19 (br m, 3H), 1.15-1.30 (br m, 3H), 1.45 (s, 9H), 3.14-3.31 (br m, 2H), 3.45-3.62 (br m, 2H), 4.33 (d, J=5.6 Hz, 1H), 4.95 (br s, 1H), 7.19-7.38 (m, 4H).

Workup

  1. stirringthe reaction mixture was stirred for 18 h
  2. temperaturerefluxed 3 h
  3. temperatureAfter cooling
  4. concentrationthe contents were concentrated on a rotary evaporator
  5. extractionThe resulting mixture was extracted three times with dichloromethane (50 mL)
  6. washwashed twice with 1 N aqueous hydrochloric acid solution (50 mL) and twice with water (50 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b85a5b05a3c74ea897b1ad95aa90b574
Source dataset
uspto-grants-2009_08
Patent number
US07576105B2

Reaction notes

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