Triethylamine → HCID 15308002, compound

HRID 355937Notes

Reaction equation

HRID 355937 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)=[O:7])=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32](Cl)(=[O:34])=[O:33].C(N(CC)CC)C>C(Cl)Cl>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]2=3)=[O:7])=[CH:23][CH:24]=1)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 761872-Chlorobenzenesulfonyl chlorideHCID 154104675-(4-Aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

Product 1

HCID 15308002HCID 15308002, compoundYield 128.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.13 g of 5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine, 0.21 g of 2-chlorobenzenesulfonyl chloride, 0.12 g of triethylamine and 5 mg of N,N-dimethylaminopyridine in 2 ml of methylene chloride is stirred at room temperature for 18 hours. The mixture is partitioned between 1N NaOH and ethyl acetate. The organic layer is washed with 50% NH4Cl and brine, dried over Na2SO4 and evaporated to give 0.26 g of the desired product as a yellow solid. MS(CI):663(M+H; C35).

Workup

  1. customThe mixture is partitioned between 1N NaOH and ethyl acetate
  2. washThe organic layer is washed with 50% NH4Cl and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-72442b9bedf541d28966b8af53f0cc04
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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