Tin tetrachloride → HCID 18430708, compound

HRID 1954269Notes

Reaction equation

HRID 1954269 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:12]=1[O:13][CH3:14])[C:7]([OH:9])=O)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[CH3:24][C:25]1[S:26][C:27]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:28][C:29]=1[CH3:30].[Sn](Cl)(Cl)(Cl)Cl>CN(C)C=O.C(Cl)Cl>[CH2:31]([C:27]1[S:26][C:25]([CH3:24])=[C:29]([CH3:30])[C:28]=1[C:7]([C:6]1[CH:10]=[C:11]([CH:15]([CH3:17])[CH3:16])[C:12]([O:13][CH3:14])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=1)=[O:9])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 24287Tin tetrachlorideHCID 65578Oxalyl chlorideHCID 102419632,3-Dimethyl-5-benzylthiopheneHCID 15895030HCID 15895030, compound

Product 1

HCID 18430708HCID 18430708, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Using 3,5-diisopropyl-p-anisic acid (5.0 g, 21.2 mmol, RN-117439-59-5), oxalyl chloride (2.2 mL, 25.4 mmol), N,N-dimethylformamide (2 drops), 2,3-dimethyl-5-benzylthiophene (4.3 g, 21.2 mmol), tin(IV) chloride (5.0 mL, 42.7 mmol), and anhydrous methylene chloride (82 mL) the title compound was prepared according to the procedure in Example 2, step 1 to give 4.1 g (45%) NMR (DMSO-d6) δ 7.47 (s, 2 H), 7.23-7.12 (m, 3 H), 7.02-6.99 (m, 2 H), 3.86 (s, 2 H), 3.73 (s, 3 H), 3.31-3.20 (m, 2 H), 2.27 (s, 3 H), 1.82 (s, 3 H), 1.15 (d, 12 H). MS(EI), [M+] 420.

Sources & evidence

ORD record
ord-b5efc1f7df554eabae1cad70250d403e
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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