Triethylamine → HCID 22291129, compound

HRID 1369506Notes

Reaction equation

HRID 1369506 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[C:11]([NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)[CH:12]=[CH:13][C:14]=1[CH3:15].[Cl:27][CH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([C:17]([NH:16][C:11]2[CH:12]=[CH:13][C:14]([CH3:15])=[C:9]([NH:8][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][C:29]([CH2:28][Cl:27])=[CH:30][CH:31]=3)[CH:10]=2)=[O:26])=[CH:19][CH:20]=1)#[N:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 22057994HCID 22057994, compound

Product 1

HCID 22291129HCID 22291129, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.55 ml) was added to a suspension of N-(3-amino-4-methylphenyl)-4-cyanobenzamide (0.40 g), 4-(chloromethyl)benzoyl chloride (0.45 g) and 4-dimethylaminopyridine (0.019 g) in methylene chloride (12 ml) and the mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was triturated with water. The resultant solid was isolated and washed in turn with 2N hydrochloric acid and a saturated aqueous sodium bicarbonate solution. The solid was dried under vacuum at 55° C. to give the required starting material (0.64 g); NMR Spectrum: (DMSOd6) 2.2 (s, 3H), 4.82 (s, 2H), 7.23 (d, 1H), 7.58 (m, 3H), 7.84 (s, 1H), 7.99 (m, 4H), 8.1 (d, 2H), 9.91 (s, 1H), 10.46 (s, 1H); Mass Spectrum: M−H− 402.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was triturated with water
  3. customThe resultant solid was isolated
  4. washwashed in turn with 2N hydrochloric acid
  5. customThe solid was dried under vacuum at 55° C.

Sources & evidence

ORD record
ord-f0e0971363c14869b9d60d917f3be8a0
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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