Butyl Chloride → HCID 14180639, compound

HRID 1164741Notes

Reaction equation

HRID 1164741 reaction equation
[OH:1][CH:2]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10].C1([O:24][C:25](=O)[NH:26][C:27]2[N:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[N:28]=2)C=CC=CC=1.C1CCN2C(=NCCC2)CC1.CCCCCl>O1CCOCC1.Cl.C(Cl)Cl>[CH3:34][O:33][C:31]1[CH:30]=[C:29]([O:35][CH3:36])[N:28]=[C:27]([NH:26][C:25]([NH:12][S:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:2]([OH:1])[C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:10])=[O:11])=[O:24])[N:32]=1

Participants

8

Reactant 4

HCID 8005Butyl ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 19863039HCID 19863039, compound

Product 1

HCID 14180639HCID 14180639, compoundYield 35.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To 0.5 g of the product of Example 6, dissolved in 30 mL of p-dioxane, was added 0.51 g of phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate followed by 0.27 mL of "DBU". The reaction was stirred for 1.5 hours, diluted with 45 mL of ice-water and acidified with 10 drops of concentrated hydrochloric acid to obtain an oily precipitate. The water was decanted from the oil and the oily residue was dissolved in methylene chloride, washed with water and brine, and finally dried (MgSO4). Filtration and concentration of the filtrate, in vacuo, yielded an oil. Trituration with a 10:1 mixture of n-chlorbutane and methylene chloride provided 0.3 g of the subject compound as an off-white solid, m.p. 152°-54°.

Workup

  1. customto obtain an oily precipitate
  2. customThe water was decanted from the oil
  3. dissolutionthe oily residue was dissolved in methylene chloride
  4. washwashed with water and brine
  5. dry with materialfinally dried (MgSO4)
  6. filtrationFiltration and concentration of the filtrate
  7. customin vacuo, yielded an oil

Sources & evidence

ORD record
ord-36e21e0d5c054ad6affd144f196024f8
Source dataset
uspto-grants-1990_03
Patent number
US04906283

Reaction notes

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