Aniline → Acetanilide

HRID 1649329Notes

Reaction equation

HRID 1649329 reaction equation
COC1C=CC(C2[CH:15](OC(=O)C)[C:14](=[O:20])[N:13](C(=O)C)[C:12]3[CH:24]=[CH:25][CH:26]=[CH:27][C:11]=3S2)=CC=1.NC1C=CC=CC=1>C(Cl)(Cl)Cl>[C:14]([NH:13][C:12]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:11]=1)(=[O:20])[CH3:15]

Participants

4

Reactant 2

HCID 6115AnilineHCID 132366692-(4'-Methoxyphenyl)-3-acetoxy-5-acetyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Product 1

HCID 904AcetanilideYield 88.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7-(3). The compound (VII) (200 mg) and aniline (63 mg) are added to chloroform (10 ml), and the mixture is stirred at room temperature for 2 hours. The chloroform solution is concentrated and subjected to thin layer chromatography using silica gel (developer, benzene:ethyl acetate=1:1) to give acetanilide (62 mg, 88.3%) and the title compound (II) (159 mg, 89.2%), m.p. 196°-198° C.

Workup

  1. concentrationThe chloroform solution is concentrated

Sources & evidence

ORD record
ord-8efb82792a954b5a885205cad3dea883
Source dataset
uspto-grants-1983_11
Patent number
US04416819

Reaction notes

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