Hydrochloric Acid → 8-chlorodibenzo[b,f][1,4]thiazepin-11(10H)-one

HRID 1725447Notes

Reaction equation

HRID 1725447 reaction equation
COC(=O)[C:4]1[CH:9]=[CH:8][C:7](Cl)=[C:6]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:5]=1[NH2:18].[CH3:20][Al](C)C.[OH2:24].[ClH:25]>C(Cl)Cl>[Cl:25][C:9]1[CH:8]=[CH:7][C:6]2[S:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:20](=[O:24])[NH:18][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 16682925TrimethylaluminumHCID 86607377HCID 86607377, compound

Product 1

HCID 8271058-chlorodibenzo[b,f][1,4]thiazepin-11(10H)-oneYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(2-amino-4-chlorophenylsulfanylbenzoic acid methyl ester (189JO11) (149 mg, 0.51 mmol) and AlMe3 (355 μL, 0.71 mmol, 2 M in toluene) in CH2Cl2 (3 mL) was stirred at ambient temperature for six days, and then water was added carefully. The mixture was diluted with CH2Cl2, and was acidified with 2 M aqueous HCl. The organic phase was separated, dried (Na2SO4), concentrated and flash chromatographed (heptane:EtOAc, 5:1-3:1) to give 38 mg (29%) of the title compound (189JO13). MS (ESI) 262 (MH+).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customflash chromatographed (heptane:EtOAc, 5:1-3:1)

Sources & evidence

ORD record
ord-354b668b859549efb5e88eafe3f29f08
Source dataset
uspto-grants-2009_02
Patent number
US07491715B2

Reaction notes

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