2-Methylbenzoyl chloride → HCID 67624001, compound

HRID 962589Notes

Reaction equation

HRID 962589 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][C:3]=1[C:4]([N:6]1[CH2:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2)=[O:5].C(N(CC)C(C)C)(C)C.[CH3:35][C:36]1[CH:44]=[CH:43][CH:42]=[CH:41][C:37]=1[C:38](Cl)=[O:39]>C(Cl)Cl>[CH:17]1[C:8]2[CH2:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[CH2:12][N:6]([C:4]([C:3]3[CH:21]=[CH:22][C:23]([NH:25][C:38](=[O:39])[C:37]4[CH:41]=[CH:42][CH:43]=[CH:44][C:36]=4[CH3:35])=[CH:24][C:2]=3[Cl:1])=[O:5])[C:7]=2[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 702762-Methylbenzoyl chlorideHCID 81531DiisopropylethylamineHCID 54166381HCID 54166381, compound

Product 1

HCID 67624001HCID 67624001, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.31 g of 5-(2-chloro-4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine and 0.15 g of N,N-diisopropylethylamine in 10 ml of methylene chloride is cooled in an ice bath while 0.18 g of 2-methylbenzoyl chloride is added. The bath is removed and the reactants stirred at room temperature for 18 hours. The mixture is washed with water, 1N HCl, water, 1M NaHCO3, brine and dried (Na2SO4). The methylene chloride is removed in vacuo to give 0.34 g of the desired product as crystalline solid, m.p. 138°-150° C. M+ =467.

Workup

  1. additionis added
  2. customThe bath is removed
  3. washThe mixture is washed with water, 1N HCl, water, 1M NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. customThe methylene chloride is removed in vacuo

Sources & evidence

ORD record
ord-c6e2c9d3d36a4d148305645cae2bbc8c
Source dataset
uspto-grants-1998_06
Patent number
US05760031

Reaction notes

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