Phosphorus sulfide (P2S5) → trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)methanethioamide

HRID 16156

Reaction equation

HRID 16156 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[Cl:15][C:16]1[CH:37]=[CH:36][C:19]2[O:20][C:21]3[CH:35]=[CH:34][CH:33]=[CH:32][C:22]=3[C@@H:23]3[C@H:28]([NH:29][CH:30]=O)[CH2:27][CH2:26][CH2:25][N:24]3[C:18]=2[CH:17]=1>O1CCOCC1>[Cl:15][C:16]1[CH:37]=[CH:36][C:19]2[O:20][C:21]3[CH:35]=[CH:34][CH:33]=[CH:32][C:22]=3[C@@H:23]3[C@H:28]([NH:29][CH:30]=[S:2])[CH2:27][CH2:26][CH2:25][N:24]3[C:18]=2[CH:17]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 86599863trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)formamide

Product 1

HCID 86599864trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)methanethioamideYield 81.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phosphorus pentasulfide (5 mg, 0.01 mmol) was added to trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)formamide (5 mg, 0.015 mmol) in dioxane. The resulting mixture was heated to reflux for 3 h. After evaporation under reduced pressure the crude compound was chromatographed on silica. Elution with toluene/ethyl acetate 85:15 gave trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)methanethioamide (2.8 mg, 51%). Data: (m/z)=345 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 h
  3. customAfter evaporation under reduced pressure the crude compound
  4. customwas chromatographed on silica
  5. washElution with toluene/ethyl acetate 85:15

Sources & evidence

ORD record
ord-1307a25a8d6f48d0945a334796242a97
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Linked notes

Loading…