2-Hydroxy-1-naphthaldehyde → 2-Cyano-3-(2-hydroxynaphth-1-yl) thioacrylamide

HRID 375804

Reaction equation

HRID 375804 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]=O.[C:14]([CH2:16][C:17]([NH2:19])=[S:18])#[N:15].C(N(C(O)C)CC)C>C(O)C>[C:14]([C:16](=[CH:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[OH:1])[C:17]([NH2:19])=[S:18])#[N:15]

Participants

5

Reactant 3

HCID 128192-Hydroxy-1-naphthaldehydeHCID 14162772-CyanoethanethioamideHCID 158948401-(Diethylamino)ethanol

Product 1

HCID 1361534722-Cyano-3-(2-hydroxynaphth-1-yl) thioacrylamideYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-hydroxy-1-naphthaldehyde (172 mg, 1 mmol), 2-cyanothioacetamide (110 mg, 1.1 mmol), N,N-diethylaminoethanol (23 mg, 0.2 mmol) and 15 ml ethanol is stirred for 30 min at reflux under nitrogen. Then the mixture is chilled, the precipitate filtered, washed with ice-cooled ethanol and dried in a vacuum-oven. Thus an almost pure title compound is obtained in 85% yield (1080 mg). Recrystallization from ethanol furnishes very pure samples.

Workup

  1. temperatureat reflux under nitrogen
  2. temperatureThen the mixture is chilled
  3. filtrationthe precipitate filtered
  4. washwashed with ice-
  5. temperaturecooled ethanol
  6. customdried in a vacuum-oven

Sources & evidence

ORD record
ord-3668e06acc7d4dadb904439418140511
Source dataset
uspto-grants-1996_01
Patent number
US05488057

Linked notes

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