Hydrochloric Acid → HCID 15077134, compound

HRID 2165992Notes

Reaction equation

HRID 2165992 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([S:7]([NH2:10])(=[O:9])=[O:8])[S:5][CH:6]=1.C[Al](C)C.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[N:20]=[C:19]([NH:25][C:26](=O)[O:27]C)[N:18]=1.Cl>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:24][O:23][C:21]1[CH:22]=[C:17]([O:16][CH3:15])[N:18]=[C:19]([NH:25][C:26]([NH:10][S:7]([C:4]2[S:5][CH:6]=[C:2]([Cl:1])[N:3]=2)(=[O:9])=[O:8])=[O:27])[N:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13314628Methyl (4,6-dimethoxypyrimidin-2-yl)carbamateHCID 15077119HCID 15077119, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 15077134HCID 15077134, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1.6 g of 4-chloro-2-thiazolesulfonamide in 100 ml methylene chloride under a nitrogen atmosphere, 4.4 ml of a 2.0M solution of trimethylaluminum in toluene was added slowly via a syringe. The reaction mixture was stirred 10 minutes; 1.9 g of methyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate was added, and the reaction mixture refluxed for 18 hours. The reaction mixture was cooled to 0°, and 55 ml of 5% hydrochloric acid was added dropwise giving a flocculant solid. The reaction mixture was extracted with 100 ml of ethyl acetate. The organic solution was washed wtih brine, dried over magnesium sulfate, filtered and the solvent evaporated. The resulting tan solid was slurried in 1-chlorobutane, collected, washed with hexane and dried giving 1.25 g of the title compound as a white solid, m.p. 182°-183°(d). IR: 2.98 and 3.25μ (NH), 5.80μ (C=O).

Workup

  1. temperaturethe reaction mixture refluxed for 18 hours
  2. temperatureThe reaction mixture was cooled to 0°
  3. customgiving a flocculant solid
  4. extractionThe reaction mixture was extracted with 100 ml of ethyl acetate
  5. washThe organic solution was washed wtih brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customcollected
  10. washwashed with hexane
  11. customdried

Sources & evidence

ORD record
ord-ad1bc67e036e4d6a8d14af442e86a8da
Source dataset
uspto-grants-1990_07
Patent number
US04943312

Reaction notes

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