Isophthaloyl chloride → HCID 1016400, compound

HRID 1350336Notes

Reaction equation

HRID 1350336 reaction equation
[CH2:1]([NH2:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.C([N:14]([CH2:17][CH3:18])CC)C.[C:19]1([C:28](Cl)=[O:29])[CH:24]=[CH:23][CH:22]=[C:21]([C:25](Cl)=[O:26])[CH:20]=1>C(Cl)Cl.Cl>[O:7]1[C:8]2[CH:9]=[CH:10][C:2]([CH2:1][NH:11][C:28](=[O:29])[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([NH:14][CH2:17][C:18]4[CH:2]=[CH:3][C:4]5[O:5][CH2:6][O:7][C:8]=5[CH:9]=4)=[O:26])[CH:20]=3)=[CH:3][C:4]=2[O:5][CH2:6]1

Participants

6

Reactant 3

HCID 7451Isophthaloyl chlorideHCID 8471TriethylamineHCID 75799Benzo-1,3-dioxole-5-methylamine

Product 1

HCID 1016400HCID 1016400, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (200 mL) was dissolved the piperonyl amine (12.8 g, 85 mmol) and triethyl amine (9.09 g, 90 mmol). To this was added in parts 1,3-benzenedicarbonyl dichloride (8.12 g, 40 mmol). The mixture was stirred at room temperature for 24 hours and then diluted with 1N hydrochloric acid (300 mL). The mixture was filtered to collect a solid. The solid was washed with 1N sodium hydroxide (50 mL) and then water (6×100 mL). The solid was dried at 65° C. for 3 hours at reduced pressure to give 15.08 g (87%) of a white solid. MS: M+1=433.3.

Workup

  1. filtrationThe mixture was filtered
  2. customto collect a solid
  3. washThe solid was washed with 1N sodium hydroxide (50 mL)
  4. customThe solid was dried at 65° C. for 3 hours at reduced pressure

Sources & evidence

ORD record
ord-9dcf67eb626246c4855791eb5c0037e5
Source dataset
uspto-grants-2007_05
Patent number
US07214712B2

Reaction notes

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