Dimethylcarbamoyl Chloride → HCID 67749065, compound

HRID 399398Notes

Reaction equation

HRID 399398 reaction equation
[N:1]1([CH:6]=[N:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[OH:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:22][N:23]([CH3:27])[C:24](Cl)=[O:25]>O1CCCC1>[CH3:22][N:23]([CH3:27])[C:24]([O:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[N:7]=[CH:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:25]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 15380932HCID 15380932, compound

Product 1

HCID 67749065HCID 67749065, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture prepared from 4-[[(1-pyrrolidinyl)methylene]amino]-3-pyridinol (3.79 g), triethylamine (4.29 mL), dimethylcarbamyl chloride (2.74 mL) and tetrahydrofuran (130 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 and drying under high vacuum and refluxing acetone for 4 hours yielded 3.55 g of crystals, m.p. 99°-100° 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
  6. customdrying under high vacuum
  7. temperaturerefluxing acetone for 4 hours

Sources & evidence

ORD record
ord-0ff007f4d28e4b6da5b2e139437386e8
Source dataset
uspto-grants-1998_10
Patent number
US05821239

Reaction notes

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