2-Thiophenecarbonyl chloride → HCID 21081970, compound

HRID 346635Notes

Reaction equation

HRID 346635 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[C:14]([C:22]#[N:23])=[C:13]2[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>N1C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[C:14]([C:22]#[N:23])=[C:13]2[N:24]1[CH2:25][CH2:26][N:27]([C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 21081971HCID 21081971, compound

Product 1

HCID 21081970HCID 21081970, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Thiophene carbonyl chloride (160 μL, 1.5 mmol) was added to a stirred solution of Compound 73 (303 mg, 1.0 mmol) in pyridine (5 mL) under argon at 0° C. The solution was allowed to come to room temperature and further stirred overnight. The solution was poured into ice water and the solids formed were filtered. The solids were washed by excess water, dried, and recrystallized by ethyl acetate to yield 341 mg (83%) of white solids. M.P. 262° C. 1H NMR (DMSO-d6): δ 3.57 (s, 3H), 3.64 (m, 4H), 3.91 (m, 4H), 7.16 (m, 1H), 7.50 (d, J=3.2 Hz, 1H), 7.62 (d, J=9.0 Hz, 1H), 7.79 (m, 2H), 7.86 (s, 1H). EIMS m/z 414 (M+1). Anal. (C20H17ClN4O2S) C, H, N.

Workup

  1. customthe solids formed
  2. filtrationwere filtered
  3. washThe solids were washed by excess water
  4. customdried
  5. customrecrystallized by ethyl acetate

Sources & evidence

ORD record
ord-5f8d356bac2548c99ecc255986abf86d
Source dataset
uspto-grants-2007_02
Patent number
US07173036B2

Reaction notes

Loading…