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Diisopropylethylamine → 3-methyl-4-(thietan-3-ylcarbamoyl)-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

HRID 1844645
Notes
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Reaction equation

HRID 1844645 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9](/[C:11](/[S:18][CH3:19])=[N:12]/[CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[S:20]1[CH2:23][CH:22]([NH2:24])[CH2:21]1.CCN(C(C)C)C(C)C.F[B-](F)(F)F.BrC1C=CC=C[N+]=1CC>ClCCl.O>[CH3:19][S:18][C:11](=[N:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:9]1[CH:8]=[CH:7][C:3]([C:4](=[O:6])[NH:24][CH:22]2[CH2:23][S:20][CH2:21]2)=[C:2]([CH3:1])[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27363002-Bromo-1-ethylpyridinium tetrafluoroborateHCID 14594132Thietan-3-amineHCID 874255662-methyl-4-[(Z)-C-methylsulfanyl-N-(trimethylsilylmethyl)carbonimidoyl]benzoic acid

Product 1

HCID 675060713-methyl-4-(thietan-3-ylcarbamoyl)-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester
Yield 12.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-4-{methylsulfanyl-[(Z)-trimethylsilanyl methylimino]methyl}-benzoic acid (Example I18) (107 mg) in dichloromethane (6 ml) was added thietan-3-ylamine (88 mg), Hünigs base (0.248 ml) and 2-bromo-1-ethyl-pyridinium tetrafluoroborate (169 mg). The reaction mixture was stirred at ambient temperature for 2 hours. Water was added and the mixture was extracted twice with dichloromethane. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:3) to give 3-methyl-4-(thietan-3-ylcarbamoyl)-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (16 mg). 1H-NMR (400 MHz, CDCl3): 7.40-7.20 (m, 3H), 6.20 (d, 1H); 5.30 (m, 1H), 3.55 (s, 2H), 3.35 (m, 2H), 3.25 (m, 2H), 2.35 (s, 3H), 1.95 (s, 3H), 0.00 (s, 9H) ppm.

Workup

  1. extractionthe mixture was extracted twice with dichloromethane
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (eluent: ethyl acetate/heptanes 1:3)

Sources & evidence

ORD record
ord-48181dce10e04fc99b133e67073d8896
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946447B2

Reaction notes

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