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Triethylamine → 1-[(2-bromophenyl)sulfanyl]-N-(cyanomethyl)cyclohexanecarboxamide

HRID 1744084
Notes
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Reaction equation

HRID 1744084 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1([C:15]([OH:17])=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CN(C(O[N:26]1N=[N:33][C:28]2C=CC=N[C:27]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.NCC#N.CCN(CC)CC>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1([C:15]([NH:33][CH2:28][C:27]#[N:26])=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11491918Aminoacetonitrile hydrochlorideHCID 222359741-[(2-Bromophenyl)sulfanyl]cyclohexanecarboxylic acid

Product 1

HCID 222358561-[(2-bromophenyl)sulfanyl]-N-(cyanomethyl)cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-[(2bromophenyl)sulfanyl]cyclohexanecarboxylic acid (77 mg, 0.24 mmol), HATU (99 mg, 0.26 mmol) and aminoacetonitrile hydrochloride (33 mg, 0.35 mmol) in DMF (3 mL) was added Et3N (0.1 mL, 0.72 mmol). The mixture was stirred overnight, then partitioned between ethyl acetate and 1 M HCl. The organic phase was washed with water, 1 M NaOH and brine, then dried over MgSO4 and concentrated to give 1-[(2-bromophenyl)sulfanyl]-N-(cyanomethyl)cyclohexanecarboxamide.

Workup

  1. custompartitioned between ethyl acetate and 1 M HCl
  2. washThe organic phase was washed with water, 1 M NaOH and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ac78328672304683824ad0b5563a54d5
Source dataset
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07012075B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes