Aniline → HCID 178477926, compound

HRID 1079345Notes

Reaction equation

HRID 1079345 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:9]1[CH2:10][S:11][C:12]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:13]=2[CH2:14][N:15]=1>C(O)C>[Cl:20][C:16]1[C:13]2[CH2:14][NH:15][C:9](=[N:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:10][S:11][C:12]=2[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 23366683HCID 23366683, compound

Product 1

HCID 178477926HCID 178477926, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of aniline (4.8 ml) in dry ethanol (10 ml) was added dropwise at room temperature to a stirred solution of 3,6-dichloro-2,5-dihydro-1,4-benzothiazepine (2.5 g) in dry ethanol (65 ml). The reaction mixture was heated under reflux for 91/2 hours, cooled to room temperature, filtered and the solvent was removed from the filtrate by evaporation at reduced pressure. The oily residue was separated into fractions by chromatography on a silica gel support using chloroform/ethanol (50:1) as eluent. Purification of those fractions containing the product by flash chromatography using ethyl acetate/hexane (2:3) as eluent gave 6-chloro-3-phenylimino-2,3,4,5-tetrahydro-1,4-benzothiazepine, which was recrystallised from ethyl acetate/hexane. Yield 0.27 g (m.p. 150°-152° C.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 91/2 hours
  3. filtrationfiltered
  4. customthe solvent was removed from the filtrate by evaporation at reduced pressure
  5. customThe oily residue was separated into fractions by chromatography on a silica gel support
  6. customPurification of those fractions
  7. additioncontaining the product by flash chromatography

Sources & evidence

ORD record
ord-c1d41df5c43b4baf8e20255a94cce818
Source dataset
uspto-grants-1996_12
Patent number
US05580866

Reaction notes

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