Triethylamine → HCID 178513362, compound

HRID 1921238Notes

Reaction equation

[F:1][C:2]([F:30])([F:29])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([S:18]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:13][CH2:12]3)=[CH:5][CH:4]=1.Cl.[NH2:32][OH:33].C(N(CC)CC)C>O1CCCC1.CO>[OH:33][NH:32][C:25](=[NH:26])[C:24]1[CH:27]=[CH:28][C:21]([S:18]([N:14]2[C:15]3[C:11](=[CH:10][C:9]([C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:30])([F:29])[F:1])=[CH:4][CH:5]=4)=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 65 °C

Procedure

517 mg 4-[5-(4-trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-benzonitrile were dissolved in a mixture of 10 ml tetrahydrofuran and 10 ml methanol. 1.68 g hydroxylamine hydrochloride were added followed by the addition of 3.35 ml triethylamine. The reaction mixture was stirred at 65° C. for eight hours. The solvents were removed in vacuo and the resulting residue poured into water and extracted five times with ethylacetate. The combined organic extracts were washed with brine, dried over MgSO4 and the solvent was evaporated in vacuo to obtain 550 mg N-hydroxy-4-[5-(4-trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-benzamidine as an oil. C22H18F3N3O3S (461,47), MS (ESI): 462.2 (M+H+).

Workup

customThe solvents were removed in vacuo
additionthe resulting residue poured into water
extractionextracted five times with ethylacetate
washThe combined organic extracts were washed with brine
dry with materialdried over MgSO4
customthe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-6ac90e94ccef498183e5ec9c26f7e746
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173674B2

Reaction notes

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