Phenothiazine → Phenothiazine-10-propionitrile

HRID 364914

Reaction equation

HRID 364914 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]

Participants

7

Reactant 4

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

Product 1

HCID 228554Phenothiazine-10-propionitrile

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 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 refluxing 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. m.p. 158°-160° C.

Workup

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

Sources & evidence

ORD record
ord-0f1b3735b74a4b36b06d6a4189be648a
Source dataset
uspto-grants-1986_08
Patent number
US04607006

Linked notes

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