Hydrochloric Acid → HCID 13824432, compound

HRID 236239Notes

Reaction equation

HRID 236239 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:10]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.C[Al](C)C.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([NH:28][C:29](=O)[O:30]C)[N:22]=1.Cl>ClCCCl>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]=[C:23]([NH:28][C:29]([NH:14][S:11]([C:10]2[C:4]3[S:3][C:2]([CH3:1])=[N:6][C:5]=3[CH:7]=[CH:8][CH:9]=2)(=[O:13])=[O:12])=[O:30])[N:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13072161Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamateHCID 138244272-Methyl-7-benzothiazolesulfonamideHCID 16682925Trimethylaluminum

Product 1

HCID 13824432HCID 13824432, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 1.5 g of the product from Example 9 in 33 mL of 1,2-dichloroethane was cooled to 0° C. under a nitrogen atmosphere and treated with 3.6 mL of trimethylaluminum (2M solution in toluene). The mixture was warmed briefly to 50°-60° C., recooled to room temperature, and treated with 1.4 g of 4-methoxy-6-methylpyrimidin-2-yl-carbamic acid, methyl ester. This reaction mixture was heated at reflux temperature for approximately 48 hours and was then cooled to 0° C. and acidified by the addition of 5% aqueous hydrochloric acid. The resulting precipitate was separated by filtration and washed with water and 1-chlorobutane. The filtrate was dried over magnesium sulfate, treated with carbon, and concentrated in vacuo to give a yellow gum. Crystallization from hot acetonitrile afforded 0.45 g of the title compound as an off-white solid, m.p. 178°-180° C.; NMR (CDCl3): δ 2.5 (3H, s), 2.8 (3 H, s), 3.9 (3H, s), 6.3 (1H, s), 7.5-7.8 (1H, br s), 7.6 (1H, t), 8.2 (2H, br d); IR(KBr): 1710 (carbonyl stretch) cm-1.

Workup

  1. temperatureThe mixture was warmed briefly to 50°-60° C.
  2. customrecooled to room temperature
  3. temperatureThis reaction mixture was heated
  4. temperatureat reflux temperature for approximately 48 hours
  5. temperaturewas then cooled to 0° C.
  6. customThe resulting precipitate was separated by filtration
  7. washwashed with water and 1-chlorobutane
  8. dry with materialThe filtrate was dried over magnesium sulfate
  9. additiontreated with carbon
  10. concentrationconcentrated in vacuo
  11. customto give a yellow gum
  12. customCrystallization from hot acetonitrile

Sources & evidence

ORD record
ord-c684f24983d3441197fbfe7e41d84659
Source dataset
uspto-grants-1987_02
Patent number
US04643759

Reaction notes

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