4-Sulphamoylbenzoyl chloride → HCID 54451491, compound

HRID 1954065Notes

Reaction equation

HRID 1954065 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C@@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[NH2:16])[CH:7]=[CH:6][C:5]=1[O:17][CH3:18])[CH3:2].[S:19]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)(=[O:22])(=[O:21])[NH2:20]>C(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]2[NH:16][C:27](=[O:28])[C:26]2[CH:30]=[CH:31][C:23]([S:19](=[O:22])(=[O:21])[NH2:20])=[CH:24][CH:25]=2)[CH:7]=[CH:6][C:5]=1[O:17][CH3:18])[CH3:2]

Participants

5

Reactant 2

HCID 70103404-Sulphamoylbenzoyl chlorideHCID 54433498HCID 54433498, compound2×

Product 1

HCID 54451491HCID 54451491, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

3.0 g of (+/-)-cis-2-ethoxy-1-methoxy-4-(2-aminocyclohexyl)benzene (compound B1) are dissolved in 40 ml of methylene chloride and 10 ml of triethylamine. A solution of 3.3 g of p-sulfamoylbenzoyl chloride in 60 ml of methylene chloride is added dropwise at RT, the mixture is extracted after stirring overnight with 100 ml each of water, 2N hydrochloric acid, saturated sodium hydrogencarbonate solution and water again. The organic phase is dried using sodium sulfate and concentrated. The residue is chromatographed on silica gel using a mixture of ethyl acetate/petroleum ether/methanol in the ratio 6/3/1. After concentration of the product fractions, 1.2 g of the title compound of m.p. 129-133° C. are obtained.

Workup

  1. extractionthe mixture is extracted
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel using
  5. additiona mixture of ethyl acetate/petroleum ether/methanol in the ratio 6/3/1

Sources & evidence

ORD record
ord-056b8c492bd64100b867515f2e73f0b3
Source dataset
uspto-grants-2000_09
Patent number
US06121279

Reaction notes

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