Dimethylcarbamoyl Chloride → HCID 67749094, compound

HRID 361337Notes

Reaction equation

HRID 361337 reaction equation
[CH2:1]([N:4]([CH:8]=[N:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[OH:16])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].C(N(CC)CC)C.[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27]>O1CCCC1>[CH3:24][N:25]([CH3:29])[C:26]([O:16][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:10]=1[N:9]=[CH:8][N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])=[O:27]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 67904807HCID 67904807, compound

Product 1

HCID 67749094HCID 67749094, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture prepared from 4-[[(dipropylamino)methylene]amino]-3-pyridinol (3.22 g), triethylamine (3.15 g), dimethylcarbamyl chloride (2.01 mL) and tetrahydrofuran (100 mL) was refluxed for 1 hour, cooled, poured directly onto a silica column and eluted successively with ethyl acetate and 5% Et3N/ethyl acetate. The eluate was concentrated and the solid was recrystallized from diethyl ether to yield 2.99 g of product, m.p. 84°-85° 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. concentrationThe eluate was concentrated
  6. customthe solid was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-5cb36ce37cd34345a063516a75c1b789
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Reaction notes

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