Triethylamine → HCID 67363188, compound

HRID 1951350Notes

Reaction equation

HRID 1951350 reaction equation
O[CH2:2][C:3]1[CH2:19][N:6]2[CH:7]=[CH:8][C:9]3[C:10]([CH:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=3)=[C:5]2[N:4]=1.O=S(Cl)[Cl:22].C(N(CC)CC)C>C(Cl)Cl>[Cl:22][CH2:2][C:3]1[CH2:19][N:6]2[CH:7]=[CH:8][C:9]3[C:10]([CH:11]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:13]=3)=[C:5]2[N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 67362707HCID 67362707, compound

Product 1

HCID 67363188HCID 67363188, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 11 (47 mg, 0.18 mmol) in dry methylene chloride (10 mL), under argon, were added SOCl2 (15 μl, 0.21 mmol) and triethylamine (29 μl, 0.21 mmol). The solution was stirred at room temperature for 45 min then the solvent was removed in vacuo. The crude product was purified by chromatography using CH2Cl2/EtOH (97/3, v/v) as eluent to give compound 12 (26 mg, 52%); mp 270-272° C.; IR (KBr) 1701, 1248, 1189 cm−1; 1H NMR (400 MHz, (acetone-d6) δ 1.41 (t, 3H, J=7 Hz), 4.41 (q, 2H, J=7 Hz), 4.86 (s, 2H), 7.20 (d, 1H, J=7 Hz), 7.52 (s, 1H), 7.90 (s, 1H), 8.28 (d, 1H, J=7 Hz), 11.63 (brs, 1H); 13C NMR (100 MHz, (acetone-d6) δ 14.7, 40.6, 61.3, 102.9, 107.9, 113.1, 114.7, 125.0, 127.5, 134.3, 140.9, 142.3, 161.5; MS m/z 279 (M++2, 9), 277 (M+, 20), 196 (43), 149 (33), 85 (63), 71 (72), 57 (100). Anal. Calcd for C13H12ClN3O2: C, 56.22; H, 4.36; N, 15.13. Found: C, 56.07; H, 4.43; N, 15.10.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-2d8195a2917a42a496cfdd9179f54e00
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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