Thionyl Chloride → HCID 9826123, compound

HRID 1635104Notes

Reaction equation

HRID 1635104 reaction equation
S(Cl)(Cl)=O.[CH2:5]([O:12][C:13]1[CH:14]=[C:15]([C@H:27]2[C@@H:36]([C:37]([OH:39])=O)[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29](=[O:40])[N:28]2[CH3:41])[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1C=CC=CC=1>[CH2:5]([O:12][C:13]1[C:18]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][C:16]2[C:37](=[O:39])[C:36]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29](=[O:40])[N:28]([CH3:41])[C:27]=3[C:15]=2[CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 131723748HCID 131723748, compound

Product 1

HCID 9826123HCID 9826123, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Thionyl chloride (8.1 mL) was added with stirring to the cis acid 12g (0.7 g, 2.1 mmol). The result was a yellowish-brown mixture that became orange within 15 min and after 30 min was red. After 4 h, the reaction mixture was diluted with benzene (25 mL) and evaporated to dryness. The brownish-red solid was recrystallized from methanol and passed through a short column (SiO2), eluting with chloroform, to give a brown solid (0.14 g, 24%): MP 198-200° C.; 1H NMR (DMSO-d6) δ8.43 (d, J=8.0 Hz, 1H), 8.16 (d, J=8.0 Hz, 1H), 7.75 (t, J=7.5 Hz, 1H), 7.39 (m, 13H), 5.34 (s, 1H), 5.29 (s, 1H), 3.93 (s, 1H); CIMS m/z (relative intensity) 474 (MH+, 100). Anal. Calcd for C31H23NO4: C, H, N.

Workup

  1. waitAfter 4 h
  2. customevaporated to dryness
  3. customThe brownish-red solid was recrystallized from methanol
  4. washeluting with chloroform

Sources & evidence

ORD record
ord-36eab103b657461f89bc422472e24286
Source dataset
uspto-grants-2003_01
Patent number
US06509344B1

Reaction notes

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