Thionyl Chloride → HCID 136592739, compound

HRID 57726Notes

Reaction equation

HRID 57726 reaction equation
O[CH2:2][C:3]1[NH:8][C:7](=[O:9])[C:6]2=[CH:10][N:11]=[C:12]([CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:5]2[N:4]=1.O=S(Cl)[Cl:21]>C(Cl)Cl>[Cl:21][CH2:2][C:3]1[NH:8][C:7](=[O:9])[C:6]2=[CH:10][N:11]=[C:12]([CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[N:5]2[N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 136592741HCID 136592741, compound

Product 1

HCID 136592739HCID 136592739, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 7 (400 mg, 1.6 mmol) in CH2Cl2 (50 mL) in ice-water bath was added SOCl2 (10 mL) dropwise. The resulting mixture was then stirred at ambient temperature overnight. The reaction mixture was concentrated in vacuo to afford compound 8 (370 mg, 86% yield) as a white solid. LC-MS: m/z 269.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 12.50 (s, 1H), 8.02 (s, 1H), 4.57 (s, 2H), 3.95 (m, 2H), 3.48 (m, 3H), 1.88 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ea31b8962e2740e2a61262c052d5fb97
Source dataset
uspto-grants-2016_09
Patent number
US09434733B2

Reaction notes

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