Potassium Hydroxide → N,N'-bis(4-anilinophenyl)-4,10-dithia-7-oxatridecanediamide

HRID 1283478

Reaction equation

HRID 1283478 reaction equation
[NH:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:18])[CH:16]=[CH2:17])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][SH:25].[OH-:26].[K+]>C(O)C>[NH:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:18])[CH2:16][CH2:17][S:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][S:25][CH2:17][CH2:16][C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)=[O:26])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 750732,2'-OxybisethanethiolHCID 22601822N-(4-Anilinophenyl)prop-2-enamide

Product 1

HCID 21518143N,N'-bis(4-anilinophenyl)-4,10-dithia-7-oxatridecanediamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 100 grams of N-(4-anilinophenyl) acrylamide in 1200 milliliters of ethanol was added 29 grams of 2-mercaptoethyl ether. A solution of 5 grams of potassium hydroxide in 50 milliliters of ethanol was added at 20°C. Within 5 minutes the temperature began to rise, reaching a maximum of 29°C. after about 15 minutes. As the temperature began to rise, product began to precipitate. The reaction mixture was stirred for 1 hour and the solid product was then filtered off and allowed to dry. There was obtained 123 grams (95 percent of theory) of product which melted at 154°-156° C.

Workup

  1. customa maximum of 29°C.
  2. customafter about 15 minutes
  3. customto precipitate
  4. filtrationthe solid product was then filtered off
  5. customto dry
  6. customThere was obtained 123 grams (95 percent of theory) of product which melted at 154°-156° C.

Sources & evidence

ORD record
ord-6b2569ff8300415cb0bed72a5c48416d
Source dataset
uspto-grants-1976_08
Patent number
US03975414

Linked notes

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