Butyl Chloride → HCID 23163052, compound

HRID 1199625Notes

Reaction equation

HRID 1199625 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([NH2:17])(=[O:16])=[O:15].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.N12CCCN=C1CCCCC2.C(Cl)CCC>C(#N)C.O.Cl>[CH3:34][O:33][C:31]1[CH:30]=[C:29]([O:35][CH3:36])[N:28]=[C:27]([NH:26][C:25]([C:13]2[C:8]([CH2:7][N:3]3[CH2:4][CH2:5][CH2:6][C:2]3=[O:1])=[C:9]([S:14]([NH2:17])(=[O:15])=[O:16])[CH:10]=[CH:11][CH:12]=2)=[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 14424374HCID 14424374, compound

Product 1

HCID 23163052HCID 23163052, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 254 mg of the product of Example 2 in 10 mL of acetonitrile, containing 275 mg of phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate, was added 0.15 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The resultant solution was stirred for 2 hours, diluted with 20 mL of water and acidified with 5 drops of concentrated hydrochloric acid. n-Butylchloride (10 mL) was added, stirred, and the white precipitate was filtered. The collected white solid was washed with a little water, suction dried and finally dried in vacuo @ 70° C. overnight to afford 200 mg of a white solid, m.p. 185°-187° C.

Workup

  1. filtrationthe white precipitate was filtered
  2. washThe collected white solid was washed with a little water, suction
  3. customdried
  4. customfinally dried in vacuo @ 70° C. overnight

Sources & evidence

ORD record
ord-bf971a9bb14346be9c727918203213ea
Source dataset
uspto-grants-1990_02
Patent number
US04902339

Reaction notes

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