Triethylamine → HCID 22291033, compound

HRID 1369526Notes

Reaction equation

HRID 1369526 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[C:11]([NH:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=[CH:13][C:14]=1[CH3:15].[Cl:25][CH2:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](Cl)=[O:31]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:17]([NH:16][C:11]1[CH:12]=[CH:13][C:14]([CH3:15])=[C:9]([NH:8][C:30](=[O:31])[C:29]2[CH:33]=[CH:34][CH:35]=[C:27]([CH2:26][Cl:25])[CH:28]=2)[CH:10]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1120264N-(3-amino-4-methylphenyl)benzamideHCID 27333243-(Chloromethyl)benzoyl chloride

Product 1

HCID 22291033HCID 22291033, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.0 ml) was added to a stirred mixture of N-(3-amino-4-methylphenyl)benzamide (3.0 g), 3-chloromethylbenzoyl chloride (2.76 g), 4-dimethylaminopyridine (0.162 g) and methylene chloride (50 ml) and the reaction mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was triturated under 2N aqueous hydrochloric acid solution. The solid so obtained was isolated, washed in turn with a saturated aqueous sodium bicarbonate solution, water and isohexane and dried under vacuum at 55° C. There was thus obtained the title compound (5.1 g); NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 4.85 (s, 2H), 7.23 (d, 1H), 7.55 (m, 5H), 7.66 (d, 1H), 7.84 (s, 1H), 7.95 (m, 3H), 8.05 (s, 1H), 9.96 (s, 1H), 10.22 (s, 1H); Mass Spectrum: M−H− 377.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was triturated under 2N aqueous hydrochloric acid solution
  3. customThe solid so obtained
  4. customwas isolated
  5. washwashed in turn with a saturated aqueous sodium bicarbonate solution, water and isohexane
  6. customdried under vacuum at 55° C

Sources & evidence

ORD record
ord-325c349321e8423980d16c79e62ec47f
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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