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Phenothiazine → Phenothiazine-10-propionitrile

HRID 2413671
Notes
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Reaction equation

HRID 2413671 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.CC(C1C(O)=C(C(C)(C)C)C=C(CCC(OCC(COC(CCC2C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=2)=O)(COC(CCC2C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=2)=O)COC(CCC2C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=2)=O)=O)C=1)(C)C>CC(C)=O.C(#N)C>[C:2]([CH2:3][CH2:4][N:25]1[C:26]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[S:18][C:19]2[C:24]1=[CH:23][CH:22]=[CH:21][CH:20]=2)#[N:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7108PhenothiazineHCID 7855Acrylonitrile2×HCID 64819Antioxidant 10102×HCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 228554Phenothiazine-10-propionitrile

Reagents, catalysts & solvents 2

HCID 180
Acetone
Solvent
HCID 6342AcetonitrileSolvent

Procedure

4 ml of Triton B (40%) (benzyltrimethylammonium hydroxide) was dropwise added to an acetonitrile solution (200 ml) containing 199 g of phenothiazine, 106 g of acrylonitrile, and a small quantity of Irganox 1010 (made by Ciba Geigy Co.). Irganox 1010 has the formula ##STR4## After refluxing for 3 hours while heating, 53 g of acrylonitrile was added thereto, followed by relfuxing for a further 2 hours while heating. After being allowed to cool, acetone was added to the reaction solution to crystallize the reaction product. Crystals thus formed were collected by filtration, and recrystallized from 900 ml of acetone to obtain 135 g of the desired compound.

Workup

  1. temperature##STR4## After refluxing for 3 hours
  2. temperaturewhile heating
  3. temperaturewhile heating
  4. temperatureto cool
  5. customto crystallize the reaction product
  6. customCrystals thus formed
  7. filtrationwere collected by filtration
  8. customrecrystallized from 900 ml of acetone

Sources & evidence

ORD record
ord-b16c8f8121544235aa15044c9676186c
Source dataset
uspto-grants-1988_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04719174

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes