Dimethylcarbamoyl Chloride → HCID 67749069, compound

HRID 361341Notes

Reaction equation

HRID 361341 reaction equation
[N:1]1([CH:7]=[N:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[OH:15])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:23][N:24]([CH3:28])[C:25](Cl)=[O:26]>O1CCCC1>[CH3:23][N:24]([CH3:28])[C:25]([O:15][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[N:8]=[CH:7][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:26]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 15380935HCID 15380935, compound

Product 1

HCID 67749069HCID 67749069, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture prepared from 4-[[(4-morpholinyl)methylene]amino]-3-pyridinol (3.04 g), triethylamine (3.19 mL), dimethylcarbamyl chloride (2.04 mL) and tetrahydrofuran (121 mL) was refluxed for 1 hour, cooled, poured directly onto a silica column and eluted successively with ethyl acetate and 5% Et3N/ethyl acetate. Recrystallization from ethyl acetate (50 mL) and drying under high vacuum and refluxing acetone overnight yielded 3.04 g of fluffy needles, m.p. 127°-129° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperaturecooled
  3. additionpoured directly onto a silica column
  4. washeluted successively with ethyl acetate and 5% Et3N/ethyl acetate
  5. customRecrystallization from ethyl acetate (50 mL)
  6. customdrying under high vacuum
  7. temperaturerefluxing acetone overnight

Sources & evidence

ORD record
ord-186f1d4255294d5481987b2d47d4d2f9
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Reaction notes

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