Thionyl Chloride → HCID 19019105, compound

HRID 1110102Notes

Reaction equation

HRID 1110102 reaction equation
O[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([N:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[C:17](=[O:24])[NH:16][C:15]3[CH:25]=[CH:26][CH:27]=[N:28][C:14]2=3)=[O:12])[CH2:6][CH2:5]1.S(Cl)([Cl:31])=O>C(Cl)(Cl)Cl>[ClH:31].[ClH:31].[Cl:31][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([N:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[C:17](=[O:24])[NH:16][C:15]3[CH:25]=[CH:26][CH:27]=[N:28][C:14]2=3)=[O:12])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 611066HCID 611066, compound

Product 1

HCID 19019105HCID 19019105, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compound 25 (110 mg, 0.22 mmol) was refluxed for 1 h with thionyl chloride (1 mL) in chloroform (4 mL). The volatile material was removed in vacuo, and the residue was basified with aqueous Na2CO3 (pH 10) and washed immediately with ether to completely remove the non polar impurity (TLC CHCl3 /CH3OH/NH4OH: 9/1/0.1, Rf 0.4). The product was extracted into CHCl3 from the cold aqueous phase and the combined CHCl3 layers were concentrated in vacuo and acidified using ether/HCl. The precipitate was dried in vacuo to yield 29 mg of 26 (25%) as a white solid: mp 188°-190° C.; 1H NMR (D20, HCl salt) δ 3.00-4.00 (m, 14 H), 7.50-7.70 (m, 3 H), 7.70-7.90 (m, 3 H), 8.40 (s, 1 H); MS (CI/NH3) m/e 400 (MH+), 212 (base), 364, 338. FAB mass spectroscopy showed peaks at mass 438 (M+ K), 422 (M+ Na), 400 (M+ H), 364, 329, 307, 289, 211, 154, and 136. The salt was stable upon storage at -20 ° C. for at least 6 months.

Workup

  1. customThe volatile material was removed in vacuo
  2. washwashed immediately with ether
  3. customto completely remove the non polar impurity (TLC CHCl3 /CH3OH/NH4OH: 9/1/0.1, Rf 0.4)
  4. extractionThe product was extracted into CHCl3 from the cold aqueous phase
  5. concentrationthe combined CHCl3 layers were concentrated in vacuo
  6. customThe precipitate was dried in vacuo

Sources & evidence

ORD record
ord-1ebab7de575e4442892a22c404694b96
Source dataset
uspto-grants-1994_06
Patent number
US05324832

Reaction notes

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