Phenothiazine → HCID 19992664, compound

HRID 344972Notes

Reaction equation

HRID 344972 reaction equation
[OH-].[CH2:2]([N+:9](C)(C)C)[C:3]1C=CC=C[CH:4]=1.[CH:13]1[C:26]2[NH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[S:18][C:17]=2[CH:16]=[CH:15][CH:14]=1.C(#N)C=C>>[CH:23]1[C:24]2[N:25]([CH:3]([CH3:4])[C:2]#[N:9])[C:26]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[S:18][C:19]=2[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 7108PhenothiazineHCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 19992664HCID 19992664, compoundYield 66%

Conditions

Temperature
80 °C

Procedure

2.5 ml of a 40% strength methanolic solution of benzyltrimethylammonium hydroxide are added dropwise to a reactor containing 100 g (0.5 moles) of phenothiazine and 530 g (10 moles) of acrylonitrile and cooled to a temperature below 10° C. The whole is heated to 80° C. for 1 hour 30 min. The excess acrylonitrile is removed by vacuum distillation. The solid is recrystallized twice from acetone. 10-Phenothiazinylproprionitrile is obtained in a 66% yield (83.9 g). M.p.: 156°-157° C.

Workup

  1. temperaturecooled to a temperature below 10° C
  2. customThe excess acrylonitrile is removed by vacuum distillation
  3. customThe solid is recrystallized twice from acetone

Sources & evidence

ORD record
ord-fe76e06ecb3043ba9be8075840662f91
Source dataset
uspto-grants-1991_10
Patent number
US05055213

Reaction notes

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