Hydrochloric Acid → HCID 18687789, compound

HRID 1873134Notes

Reaction equation

HRID 1873134 reaction equation
I[C:2]1[CH:3]=[C:4]([C:11]2[C:20]3[C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[S:23][C:19]=3[CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][CH:15]=[CH:16]3)[CH:5]=[C:6](I)[C:7]=1[O:8][CH3:9].[Cu][C:29]#[N:30].O.Cl.[CH3:33][N:34]1CCCC1=O>>[CH:27]1[C:21]2[C:20]3[C:11]([C:4]4[CH:5]=[C:6]([C:29]#[N:30])[C:7]([O:8][CH3:9])=[C:2]([CH:3]=4)[C:33]#[N:34])=[C:12]4[C:17](=[CH:18][C:19]=3[S:23][C:22]=2[CH:24]=[CH:25][CH:26]=1)[CH:16]=[CH:15][CH:14]=[CH:13]4

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 15481247HCID 15481247, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 18687789HCID 18687789, compoundYield 82%

Conditions

Temperature
150 °C

Procedure

A suspension of 11-(3,5-diiodo-4-methoxy-phenyl)-benzo[b]naphtho[2,3-d]thiophene (4.55 g, 7.68 mmol) and copper (I) cyanide 3.13 g, 38.4 mmol) in 1-methyl-2-pyrrolidinone (18 mL) was heated in an 150° C. oil bath under a dry nitrogen atmosphere. After 1 h the solution was added to water (200 mL) and acidified with 10% aqueous HCl. The solid was filtered and flash chromatographed (silica gel: eluent: methylene chloride) to provide the title compound as a yellow solid (2.47 g, 82%): mp 214-215° C.: MS (EI): [M+], 390 (100%, MI); Anal. Calc. for C25H14N2OS: C, 76.90, H, 3.61, N, 7.17. Found: C, 76.48, H, 3.46, N, 7.17.

Workup

  1. filtrationThe solid was filtered
  2. customflash chromatographed (silica gel: eluent: methylene chloride)

Sources & evidence

ORD record
ord-073d0525c8ee4fdc8313f6bc7cb06e32
Source dataset
uspto-grants-2000_08
Patent number
US06110962

Reaction notes

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