2-Chloro-p-toluidine → HCID 178426549, compound

HRID 1898463Notes

Reaction equation

HRID 1898463 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[NH:8][C:9]1[NH:10][C:11]2[C:17]3[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[C:15]([C:23]([O:25]C)=O)=[CH:14][C:12]=2[N:13]=1.[Cl:28][C:29]1[CH:35]=[C:34]([CH3:36])[CH:33]=[CH:32][C:30]=1[NH2:31].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:28][C:29]1[CH:35]=[C:34]([CH3:36])[CH:33]=[CH:32][C:30]=1[NH:31][C:23]([C:15]1[C:16]2[O:20][C:19]([CH3:21])([CH3:22])[CH2:18][C:17]=2[C:11]2[NH:10][C:9]([NH:8][C:7]3[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=3[Cl:27])=[N:13][C:12]=2[CH:14]=1)=[O:25]

Participants

5

Reactant 3

HCID 120072-Chloro-p-toluidineHCID 16682925TrimethylaluminumHCID 178496992HCID 178496992, compound

Product 1

HCID 178426549HCID 178426549, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared following the procedure described for Example-137 by using methyl 2-[(3,5-dichloropyridin-4-yl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylate (Step-1 of Intermediate-3, 0.100 g, 0.245 mmol), 2-chloro-4-methylaniline (0.052 g, 0.361 mmol), trimethyl aluminium (2M solution in toluene) (0.5 mL), dry toluene (5.0 mL) at room temperature to afford 0.030 g of the desired product. 1HNMR (DMSO-d6): δ 1.55 (s, 6H), 2.26 (s, 3H), 3.08 (s, 2H), 7.16 (t, J=7.8 Hz, 1H), 7.30 (s, 1H), 7.36 (s, 1H), 8.43 (s, 2H), 8.46 (s, 1H), 10.09 (s, 1H), 10.99 (br s, 1H), 11.52 (br s, 1H); MS [M+H]+: 517.97.

Workup

  1. customThe title compound was prepared
  2. customat room temperature

Sources & evidence

ORD record
ord-af237e4a680c4a37810c8cccddb35d85
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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