Triethylamine → HCID 178522513, compound

HRID 1639555Notes

Reaction equation

HRID 1639555 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[NH:12][C:11]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:10]=3[N:9]=2)=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[S:33](Cl)(=[O:35])=[O:34]>CC(C)=O.C(OCC)C>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[S:33]([O:17][C:15]1[CH:14]=[CH:13][C:11]2[NH:12][C:8]([NH:7][C:5](=[O:6])[NH:4][CH:1]3[CH2:3][CH2:2]3)=[N:9][C:10]=2[CH:16]=1)(=[O:35])=[O:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5221832,6-Dichlorobenzenesulfonylchloride2×HCID 178522504HCID 178522504, compound

Product 1

HCID 178522513HCID 178522513, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 300 mg of 1-cyclopropyl-3-(5-hydroxy-1H-benzimidazol-2-yl)urea in 100 cm3 of acetone are added 186 mg of triethylamine and 349 mg of 2,6-dichlorobenzenesulfonyl chloride. After stirring overnight at a temperature in the region of 20° C., 90 mg of 2,6-dichlorobenzenesulfonyl chloride are added and the mixture is stirred for a further 24 hours. The reaction medium is evaporated to dryness under reduced pressure (2 kPa). The residue is taken up in 50 cm3 of water and then extracted with three times 40 cm3 of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure (0.5 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/methanol (96.5/3.5 by volume)], the product obtained is solidified in 10 cm3 of diethyl ether and then filtered off, washed with three times 5 cm3 of diethyl ether and dried under reduced pressure over phosphorus pentoxide. 130 mg of 2-[(cyclopropylcarbamoyl)amino]-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate are obtained in the form of a cream-coloured powder, the characteristics of which are as follows:

Workup

  1. additionare added
  2. customThe reaction medium is evaporated to dryness under reduced pressure (2 kPa)
  3. extractionextracted with three times 40 cm3 of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure (0.5 kPa)
  7. customAfter flash chromatography on a column of silica [eluent: dichloromethane/methanol (96.5/3.5 by volume)], the product obtained
  8. filtrationfiltered off
  9. washwashed with three times 5 cm3 of diethyl ether
  10. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-acebc7af9d0f4e43867853db36d64e17
Source dataset
uspto-grants-2012_02
Patent number
US08110571B2

Reaction notes

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