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Benzaldehyde → HCID 58504128, compound

HRID 2407666
Notes
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Reaction equation

HRID 2407666 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.N=C=N.[C:14]1([C:20]2[CH:24]=[C:23]([CH2:25][N:26]3[CH2:31][CH2:30][CH:29]([CH2:32][NH2:33])[CH2:28][CH2:27]3)[O:22][N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)C1C=CC=CC=1.C([NH+](CC)CC)C.C(=O)([O-])[O-]>ClC(Cl)C.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:33][CH2:32][CH:29]2[CH2:28][CH2:27][N:26]([CH2:25][C:23]3[O:22][N:21]=[C:20]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:24]=3)[CH2:31][CH2:30]2)=[O:10])=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 240BenzaldehydeHCID 19660Carbonate IonHCID 160435CarbodiimideHCID 1385867TriethylammoniumHCID 27628725-Chloro-2-picolinic acidHCID 58504252HCID 58504252, compound

Product 1

HCID 58504128
HCID 58504128, compound
Yield 39.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 5-chloropicolinic acid (43 mg) and N-cyclohexylcarbodiimide-N′-propyloxymethyl polystyrene resin (PS-Carbodiimide: Argonaut Technologies catalog number 80,037-1; 354 mg) in dichloroethane (4 mL) was shaken for 45 minutes. The reaction was shaken for 45 minutes more after the addition of N,N-dimethylformamide (0.1 mL). The compound prepared in Example 9 (50 mg) was added and the mixture was shaken overnight. Benzaldehyde polystyrene resin (PS-benzaldehyde: Argonaut Technologies catalog number 80,036-2; 184 mg) was then added and the reaction was shaken for 3.5 hours. Macroporous triethylammonium methylpolystyrene carbonate (MP-carbonate: Argonaut Technologies catalog number 80,026-9; 202 mg) was added and the reaction was shaken for 1.5 hours more. The mixture was then filtered and concentrated to obtain the title compound (30 mg) having the following physical data.

Workup

  1. stirringThe reaction was shaken for 45 minutes
  2. stirringthe mixture was shaken overnight
  3. stirringthe reaction was shaken for 3.5 hours
  4. stirringthe reaction was shaken for 1.5 hours more
  5. filtrationThe mixture was then filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-275fab5412d248d3990b3b2d05ac79ae
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08809538B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes