Dimethylcarbamoyl Chloride → HCID 67749078, compound

HRID 362207Notes

Reaction equation

HRID 362207 reaction equation
[N:1]1([CH:8]=[N:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[OH:16])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.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:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:27]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 15380934HCID 15380934, compound

Product 1

HCID 67749078HCID 67749078, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture prepared from 4-[[(hexahydro-azepin-1-yl)methylene]amino]-3-pyridinol (2.9 g), triethylamine (2.86 ml), dimethylcarbamyl chloride (1.83 ml) and tetrahydrofuran (85 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 dried under high vacuum to obtain 3.88 g of oil. The oil solidified in a refrigerator over the weekend, and was triturated with cold pentane to yield 3.31 g of solid, m.p. 68°-70° 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. customdried under high vacuum

Sources & evidence

ORD record
ord-104b544297094c8fbf630e071cdf7e02
Source dataset
uspto-grants-1999_02
Patent number
US05869480

Reaction notes

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