Hydrochloric Acid → HCID 13472243, compound

HRID 1789134Notes

Reaction equation

HRID 1789134 reaction equation
[CH2:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([S:10]([NH2:13])(=[O:12])=[O:11])[C:4]=2[CH2:3][S:2]1(=O)=O.C[Al](C)C.[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([NH:30][C:31](=O)[O:32]C)[N:23]=1.Cl>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:29][O:28][C:26]1[CH:27]=[C:22]([O:21][CH3:20])[N:23]=[C:24]([NH:30][C:31]([NH:13][S:10]([C:9]2[C:4]3[CH2:3][S:2][CH2:1][C:5]=3[CH:6]=[CH:7][CH:8]=2)(=[O:12])=[O:11])=[O:32])[N:25]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13314628Methyl (4,6-dimethoxypyrimidin-2-yl)carbamateHCID 13472239HCID 13472239, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 13472243HCID 13472243, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 0.74 g of the sulfonamide prepared in Example 13 in 50 ml of methylene chloride was cooled to 10° to 15° under nitrogen, and 1.7 ml of a 2M solution of trimethylaluminum in toluene was added slowly. The suspension was allowed to warm to room temperature, 0.67 g of methyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate was added, and the reaction mixture was heated at reflux overnight. The turbid solution was cooled to 0°-5° and 50 ml of 5% hydrochloric acid was added dropwise. The two-phase suspension was allowed to warm to ambient temperature, then filtered. The solid was washed with 1-chlorobutane and dried giving 0.31 g of 1,3-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzo[c]thiophene-4-sulfonamide, 2,2-dioxide, m.p. 170°-173°(d).

Workup

  1. temperaturewas cooled to 10° to 15° under nitrogen
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux overnight
  4. temperatureThe turbid solution was cooled to 0°-5°
  5. temperatureto warm to ambient temperature
  6. filtrationfiltered
  7. washThe solid was washed with 1-chlorobutane
  8. customdried

Sources & evidence

ORD record
ord-063544486b52402f879594b5f17cda45
Source dataset
uspto-grants-1987_08
Patent number
US04687508

Reaction notes

Loading…