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Dimethylformamide → HCID 22116938, compound

HRID 355594
Notes
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Reaction equation

HRID 355594 reaction equation
[CH3:1][C:2]1([CH3:26])[C:6](=[O:7])[N:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[C:4](=[O:20])[N:3]1[CH2:21][CH2:22][CH2:23][CH2:24][OH:25].[C:27](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C.CN(C)C=O>CN(C)C1C=CN=CC=1.CCOCC.O>[O:20]=[C:4]1[N:3]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:2]([CH3:26])([CH3:1])[C:6](=[O:7])[N:5]1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:17])([F:18])[F:19])[CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 1329814-(3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile

Product 1

HCID 22116938HCID 22116938, compoundYield 76.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 962WaterSolvent
HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

370 mg of the product of Example 58, 307 mg of trityl chloride in the presence of 10 mg of 4-dimethylaminopyridine, 0.25 ml of triethylamine and 4 ml of dimethylformamide were stirred at ambient temperature for 16 hours. The mixture was heated to 40° C. for 4 hours, poured into water and extraction was carried out with ether. The extracts were washed with water and dried and the solvent was eliminated under reduced pressure. The residue was chromatographed on silica (eluant: cyclohexane--ethyl acetate 75-25) to obtain 467 mg of the expected product with a Rf=0.25.

Workup

  1. washThe extracts were washed with water
  2. customdried
  3. customThe residue was chromatographed on silica (eluant: cyclohexane--ethyl acetate 75-25)

Sources & evidence

ORD record
ord-5e1f7b717f3749b6b581c38ca2984e61
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
USRE035956

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes