Hydrochloric Acid → HCID 178503123, compound

HRID 2356349Notes

Reaction equation

HRID 2356349 reaction equation
Cl.[C:2](/[C:4](/[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)=[O:20])=[C:5](/[NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=1)\[S:6][CH3:7])#[N:3].C([OH:31])C>ClCCl>[OH:31][C:2]1[C:4]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[O:20])=[C:5]([S:6][CH3:7])[N:8]=[C:9]([C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 58837304HCID 58837304, compound

Product 1

HCID 178503123HCID 178503123, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dry HCl gas was passed through a solution of N-[(1E)-2-Cyano-3-[(4-methylphenyl)amino]-1-(methylthio)-3-oxoprop-1-en-1-yl]-4-(methylthio)benzamide (2 g, 5 mmol, prepared according to the procedure described in preparation 1) in ethanol (50 ml) at 0° C. for 4 hours. The reaction mixture was then refluxed for 4 hours until completion; subsequently the resultant solid was filtered and washed with ethanol. The solid thus obtained was suspended in dichloromethane (50 ml), filtered, and finally dried under vacuum to yield the title compound (1.8 g, 90%, purity 99.78% by HPLC), m.p.: 302-305° C. 1H-NMR (CDCl3) δ (ppm): 2.29 (s, 3H), 2.33 (s, 3H), 2.63 (s, 3H), 7.12-7.14 (d, 2H), 7.23-7.26 (m, 2H), 7.47-7.49 (d, 2H), 8.13-8.15 (d, 2H), 11.38 (s, 1H, D2O exchangeable), 12.45 (s, 1H, D2O exchangeable). IR (KBr) cm−1: 3436, 3320, and 1646. MS m/z: 398.1(M++1).

Workup

  1. customprepared
  2. temperatureThe reaction mixture was then refluxed for 4 hours until completion
  3. filtrationsubsequently the resultant solid was filtered
  4. washwashed with ethanol
  5. customThe solid thus obtained
  6. filtrationfiltered
  7. customfinally dried under vacuum

Sources & evidence

ORD record
ord-de8526af3cb049cebf9172fdce615548
Source dataset
uspto-grants-2010_07
Patent number
US07759350B2

Reaction notes

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