Thionyl Chloride → HCID 9893279, compound

HRID 1635105Notes

Reaction equation

HRID 1635105 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][C:32]([O:42][CH3:43])=[C:33]([O:40][CH3:41])[CH:34]=3)[C:29](=[O:44])[N:28]2[CH3:45])[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][C:32]([O:42][CH3:43])=[C:33]([O:40][CH3:41])[CH:34]=4)[C:29](=[O:44])[N:28]([CH3:45])[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 86758805HCID 86758805, compound

Product 1

HCID 9893279HCID 9893279, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Thionyl chloride (15 mL) was added with stirring to the cis acid 12h (1.2 g, 2.2 mmol). The result was an orange mixture that became dark red within 15 min. After 6 h, the reaction mixture was diluted with benzene (25 mL) and evaporated to dryness. Chloroform (7 mL) was added to the purple solid and the solid was collected and washed with ether to give a light purple solid (0.75 g, 64%): mp 238-240° C.; IR (thin film) 3027, 2963, 1685, 1649, 1493, 1458, 1252, 1203, 1088, 1014 cm−1; 1H NMR (CDCl3, 300 MHz) δ7.96 (s, 1H), 7.62 (s, 1H), 7.38 (m, 1H), 7.21 (s, 1H), 7.11 (s, 1H), 5.23 (d, 4H, J=5.2 Hz), 4.02 (s, 3H) 3.95 (s, 3H), 3.81 (s, 3H); CIMS m/z (relative intensity) 534 (MH+, 22). Anal. Calcd for C33H27NO6: C, H, N.

Workup

  1. waitAfter 6 h
  2. customevaporated to dryness
  3. additionChloroform (7 mL) was added to the purple solid
  4. customthe solid was collected
  5. washwashed with ether

Sources & evidence

ORD record
ord-787eaf17d01b40699862c08707c3ef2a
Source dataset
uspto-grants-2003_01
Patent number
US06509344B1

Reaction notes

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