2,3-Dimethylaniline → 4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl) carbonyl]-N-(2,3-dimethylphenyl]benzamide

HRID 362399Notes

Reaction equation

HRID 362399 reaction equation
[CH:1]1[C:11]2[CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH2:7][N:6]([C:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=3)=[O:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:27][C:28]1[C:34]([CH3:35])=[CH:33][CH:32]=[CH:31][C:29]=1[NH2:30]>C(N(CC)CC)C>[CH:1]1[C:11]2[CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[CH2:7][N:6]([C:16]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH:30][C:29]4[CH:31]=[CH:32][CH:33]=[C:34]([CH3:35])[C:28]=4[CH3:27])=[O:23])=[CH:20][CH:19]=3)=[O:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 68932,3-DimethylanilineHCID 538022444-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]benzoyl chloride

Product 1

HCID 153079924-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl) carbonyl]-N-(2,3-dimethylphenyl]benzamideYield 98.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

As described for Example 123, a mixture of 0.361 g of 4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]benzoyl chloride, 0.101 g of triethylamine and 0.145 g of 2,3-dimethylaniline is stirred for 1.5 hr. and worked up to give 0.44 g of crystals, m.p. 248°-251° C.

Sources & evidence

ORD record
ord-bbc48ec6b5bf4ee085444be7a34022ba
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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