Triethylamine → 10,11-Dihydro-10-(4-nitrobenzoyl)dibenz[b,f][1,4]thiazepine

HRID 1598685Notes

Reaction equation

HRID 1598685 reaction equation
[CH:1]1[C:6]2[CH2:7][NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[N+:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)([O-:25])=[O:24]>ClCCl.CN(C1C=CN=CC=1)C>[N+:23]([C:26]1[CH:27]=[CH:28][C:29]([C:30]([N:8]2[CH2:7][C:6]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]2=3)=[O:31])=[CH:33][CH:34]=1)([O-:25])=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 1231048210,11-Dihydrodibenzo(b,f)(1,4)thiazepine

Product 1

HCID 5457007210,11-Dihydro-10-(4-nitrobenzoyl)dibenz[b,f][1,4]thiazepineYield 112.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.6 g of 10,11-dihydrodibenz[b,f][1,4]thiazepine in 30 ml of dichloromethane is added 0.1 g of 4-(N,N-dimethylamino)pyridine, 4 ml of triethylamine and 1.0 g of 4-nitrobenzoyl chloride and the mixture is stirred for 16 hours. The mixture is poured into ice-water and extracted with 3×150 ml of dichloromethane. The combined organic extract is washed with water, 2N HCl, 2N Na2CO3, water and dried (MgSO4). The solvent is removed in vacuo and the product (2.6 g) purified by chromatography on silica gel with hexane-ethyl acetate (4:1) as eluent to give 2.2 g of crystals, m.p. 147°-149° C.

Workup

  1. extractionextracted with 3×150 ml of dichloromethane
  2. extractionThe combined organic extract
  3. washis washed with water, 2N HCl, 2N Na2CO3, water
  4. dry with materialdried (MgSO4)
  5. customThe solvent is removed in vacuo
  6. customthe product (2.6 g) purified by chromatography on silica gel with hexane-ethyl acetate (4:1) as eluent

Sources & evidence

ORD record
ord-c7754aae8ea94f909eac126e45534d6e
Source dataset
uspto-grants-1998_04
Patent number
US05739128

Reaction notes

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