Dimethylcarbamoyl Chloride → HCID 67749094, compound

HRID 399397Notes

Reaction equation

HRID 399397 reaction equation
[CH2:1]([N:4]([CH:8]=[N:9]C1C(O)=CC=CN=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[CH2:17]([N:19](CC)CC)C.[CH3:24][N:25]([CH3:29])[C:26](Cl)=[O:27].[O:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH3:24][N:25]([CH3:29])[C:26]([O:30][C:31]1[CH:17]=[N:19][CH:34]=[CH:33][C:32]=1[N:9]=[CH:8][N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH3:7])=[O:27]

Participants

5

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 86753209HCID 86753209, compound

Product 1

HCID 67749094HCID 67749094, compound

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-ba039beb17b14cddad9406caf17faff0
Source dataset
uspto-grants-1998_10
Patent number
US05821239

Reaction notes

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