Dimethylformamide → HCID 9813609, compound

HRID 224345Notes

Reaction equation

HRID 224345 reaction equation
Br[C:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2S[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:20]([Cu])#[N:21].CN(C)C=O.[NH4+].[OH-]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[O:9]=[C:8]1[C:2]([C:20]#[N:21])=[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]2[C:6](=[CH:5][CH:13]=[CH:12][CH:11]=2)[NH:7]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 12535975HCID 12535975, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 9813609HCID 9813609, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

A stirred mixture of 10 g (0.030 mole) of 3-bromo-2-phenyl-1,5-benzothiazepin-4(5H)-one from part A, 10 g (0.11 mole) of CuCN, and 75 ml of dimethylformamide is treated with 1 ml of pyridine, heated, and the resulting dark solution refluxed for 2 hours. After cooling, the reaction mixture is poured into a vigorously stirred mixture of 600 ml of ice-water, 600 ml of concentrated NH4OH, and 300 ml of CHCl3. Stirring is continued until essentially 2 clear layers are obtained. The layers are separated and the blue aqueous NH4OH layer is extracted with additional CHCl3 (4×150 ml). The combined organic layers are washed with 10% NH4OH (2×150 ml), then with 150 ml of H2O, dried (MgSO4), and the solvent evaporated (finally at 1 mm. pressure to remove dimethylformamide) to give 5.9 g of a reddish, partly solid residue. The latter is crystallized from 60 ml of MeCN to give 2.2 g (30%) of a pale yellow solid, m.p. 263°-265°(dec.).

Workup

  1. temperatureheated
  2. temperaturethe resulting dark solution refluxed for 2 hours
  3. temperatureAfter cooling
  4. customare obtained
  5. customThe layers are separated
  6. extractionthe blue aqueous NH4OH layer is extracted with additional CHCl3 (4×150 ml)
  7. washThe combined organic layers are washed with 10% NH4OH (2×150 ml)
  8. dry with materialwith 150 ml of H2O, dried (MgSO4)
  9. customthe solvent evaporated (finally at 1 mm
  10. custompressure to remove dimethylformamide)
  11. customto give 5.9 g of a reddish, partly solid residue
  12. customThe latter is crystallized from 60 ml of MeCN

Sources & evidence

ORD record
ord-8e09100732ce4d43855824fc1477cfb3
Source dataset
uspto-grants-1980_11
Patent number
US04232027

Reaction notes

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