1,1'-Carbonyldiimidazole → HCID 136372361, compound

HRID 449783Notes

Reaction equation

HRID 449783 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([S:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH3:20])[CH:14]=2)[C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.O[N:34]=[C:35]([NH2:45])[C:36]1[CH:41]=[C:40]([CH3:42])[C:39]([OH:43])=[C:38]([CH3:44])[CH:37]=1>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([S:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH3:20])[CH:14]=2)[C:9]2[O:11][N:45]=[C:35]([C:36]3[CH:41]=[C:40]([CH3:42])[C:39]([OH:43])=[C:38]([CH3:44])[CH:37]=3)[N:34]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 67772164HCID 67772164, compoundHCID 136087281HCID 136087281, compound

Product 1

HCID 136372361HCID 136372361, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-(3-Chlorophenyl)-2-((3,4-dimethylphenyl)thio)acetic acid (3.00 g, 9.78 mmol) was dissolved in dichloroethane, then carbonyldiimidazole (2.00 g, 12.35 mmol) was added, the resulting reaction mixture was stirred for 10 minutes, N′,4-dihydroxy-3,5-dimethylbenzimidamide crude (prepared according to Diana, Guy D et al. Journal of Medicinal Chemistry, 1994, vol. 37 (15) p. 2421-2436) (1.80 g, 9.99 mmol) was added. The reaction mixture was stirred for 30 minutes, then concentrated. Flash chromatography (40% EtOAc/Hex) gave the desired adduct which was dissolved in xylene (10 mL) and heated to 125° C. for 30 minutes, then cooled. Flash chromatography (20% EtAc/Hex) gave Intermediate 4.

Workup

  1. customthe resulting reaction mixture
  2. additionwas added
  3. stirringThe reaction mixture was stirred for 30 minutes
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-491484d538e84b94baf4bb546ef08cd0
Source dataset
uspto-grants-2013_07
Patent number
US08486918B2

Reaction notes

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