Toluene → HCID 20250608, compound

HRID 1284881Notes

Reaction equation

HRID 1284881 reaction equation
Cl.[NH:2]([CH2:9][C:10]1[C:11](=[O:36])[C:12]2[C:17]([C:18](=[O:35])[C:19]=1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:37](Cl)([Cl:39])=[O:38].C1(C)C=CC=CC=1>ClCCl.C(N(C(C)C)CC)(C)C>[C:3]1([N:2]([CH2:9][C:10]2[C:11](=[O:36])[C:12]3[C:17]([C:18](=[O:35])[C:19]=2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:37]([Cl:39])=[O:38])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 20250614HCID 20250614, compound

Product 1

HCID 20250608HCID 20250608, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

2-Anilinomethyl-3-pentadecyl-1,4-naphthoquinone hydrochloride (9.25 g, 18.1 mmol) was dissolved in dichloromethane (100 ml). A 12 percent solution of phosgene in toluene (45 ml, 54.4 mmol) and diisopropylethylamine (50 ml) were added and the resulting solution was stirred at room temperature for about 15 minutes. The solution was then concentrated under reduced pressure and the residue was taken up in dichloromethane. The solution was washed with 2N hydrochloric acid, dried over anhydrous magnesium sulfate, filtered, and concentrated. The product was used as a crude oil in the preparation of the above PRDR.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. washThe solution was washed with 2N hydrochloric acid
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customin the preparation of the above PRDR

Sources & evidence

ORD record
ord-7d886bd55b634c879b4f190c5451155a
Source dataset
uspto-grants-1986_01
Patent number
US04564577

Reaction notes

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