1,1'-Thiocarbonyldiimidazole → HCID 131718300, compound

HRID 1197630Notes

Reaction equation

HRID 1197630 reaction equation
[C:1]([O:9][CH2:10][C@H:11]1[O:25][C@@:14]([O:23][CH3:24])([C:15]([CH3:22])([SiH3:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@@:13]([CH3:27])(O)[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=S>ClCCCl>[C:1]([O:9][CH2:10][C@H:11]1[O:25][C@@:14]([O:23][CH3:24])([C:15]([CH3:22])([SiH3:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[C@@H:13]([CH3:27])[CH2:12]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 131718301HCID 131718301, compound

Product 1

HCID 131718300HCID 131718300, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 3.8 g of the compound of Step 1A and thiocarbonyldiimidazole (7.0 g) in 1,2-dichloroethane (75 mL) was refluxed for 3 days and then worked up and deoxygenated as described above, Step 8A, Example 1. Yield of product was 1.2 g. 1H NMR (CDCl3) d: 8.05 (dm, 2H), 7.56 (m, 1H), & 7.44 (m, 1H, 2H) (6-O-benzoate hydrogens), 4.48 (m, 1H, H-5), 4.36 (dd, 1H, H-6a, J6a,5 =Hz, J6a,b =Hz), 4.27 (dd, 1H, H-6b, J6b,5 =Hz), 3.75 (d, 1H, H-1a, J1a,b =11.0 Hz), 3.57 (d, 1H, H-1b), 3.28 (s, 3 H. OMe), 2.17 (m, 2H, H-3a, H-4a), 1.95 (m, 1H, H-3β ), 1.70 (m, 1H, H-4β), 0.90 (s, 9H, (Me)3 -}, 0.06 (2×s, 6H, (Me)2 -Si}.

Workup

  1. customdeoxygenated

Sources & evidence

ORD record
ord-d3dfbbf229f44446a6b7f22f6afbc238
Source dataset
uspto-grants-1994_01
Patent number
US05276143

Reaction notes

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