Hydrochloric Acid → HCID 12972352, compound

HRID 1278793Notes

Reaction equation

HRID 1278793 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[CH3:8][C:9]1[S:13][C:12]2[CH:14]=[C:15]3[C:20](=[C:21]([C:22]4[CH:27]=CC(O)=[CH:24][CH:23]=4)[C:11]=2[C:10]=1[CH3:29])[CH:19]=[CH:18][CH:17]=[CH:16]3.Cl>N1C=CC=CC=1>[CH3:8][C:9]1[S:13][C:12]2[CH:14]=[C:15]3[C:20](=[C:21]([C:22]4[CH:27]=[CH:6][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:24][CH:23]=4)[C:11]=2[C:10]=1[CH3:29])[CH:19]=[CH:18][CH:17]=[CH:16]3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 9944310HCID 9944310, compound

Product 1

HCID 12972352HCID 12972352, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.68 mL, 7.20 mmol) was added to a 0° C., stirred solution of 4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol (2.0 g, 6.57 mmol) in pyridine (8.6 mL). After 17 h the reaction mixture was added to 5% aqueous HCl and the resulting solid was filtered and washed with 5% aqueous HCl, water and triturated with pet. ether. It was then dried in vacuo to provide the title compound as a white solid (1.99 g, 88%): mp: 147-150° C.; NMR (DMSO-d6); δ 8.49 (s, 1H), 7.94 (d, J=8 Hz, 1H), 7.46 (ddd, J=8, 6, 2, 1H), 7.38 (ddd, J=8, 1, 1 Hz, 1H), 7.39-7.34 (m, 2H), 7.28 (d, J=8 Hz, 2H), 6.90 (d, J=9 Hz, 2H), 2.40 (d, J=1 Hz, 3H), 2.34 (s, 3H), 1.57 (d, J=1 Hz, 3H); MS (EI): 346 (90%, MI), 304 (100%); Anal. Calc. for C22H18O2S: C, 76.27, H, 5.34, N. 0.00. Found: C, 75.88, H. 5.04, N, 0.28.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with 5% aqueous HCl, water
  3. customtriturated with pet. ether
  4. customIt was then dried in vacuo

Sources & evidence

ORD record
ord-860717e2ca6b4cd4baef1f1a35335c88
Source dataset
uspto-grants-2002_09
Patent number
US06444670B2

Reaction notes

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