Methyl 2,2,2-trichloroacetimidate → 2-(2-Trichloromethyl-1H-benzoimidazole-5-sulfonyl)-ethanol

HRID 18522

Reaction equation

HRID 18522 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:12][CH2:13][OH:14])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[NH2:8].CO[C:17](=N)[C:18]([Cl:21])([Cl:20])[Cl:19]>C(O)(=O)C.C1(C)C=CC=CC=1>[Cl:19][C:18]([Cl:21])([Cl:20])[C:17]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([S:9]([CH2:12][CH2:13][OH:14])(=[O:11])=[O:10])=[CH:3][C:2]=2[N:1]=1

Participants

5

Reactant 2

HCID 100479Methyl 2,2,2-trichloroacetimidateHCID 155969553,4-Diamino-benzene-sulfonylethan-2-ol

Product 1

HCID 1785274142-(2-Trichloromethyl-1H-benzoimidazole-5-sulfonyl)-ethanol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

500 mg (2.31 mmol) 3,4-diamino-benzene-sulfonylethan-2-ol were dissolved in 10 mL concentrated acetic acid. 0.4 mL (1.4 equiv.) methyl-2,2,2-trichloroacetimidate were added slowly and the resulting mixture was stirred at room temperature for 4 h. The mixture was diluted with 100 mL toluene and the solvent was removed under reduced pressure. The residue was rinsed with toluene, filtered and dried under vacuo to give a brown crystalline solid pure enough for all further reactions. Yield: 680 mg MS (ES+): m/e=345, chloro pattern.

Workup

  1. customthe solvent was removed under reduced pressure
  2. washThe residue was rinsed with toluene
  3. filtrationfiltered
  4. customdried under vacuo
  5. customto give a brown crystalline solid pure enough for all further reactions

Sources & evidence

ORD record
ord-defa08f4eaed4ef6b84a8a36d7d5959a
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Linked notes

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