Sodium hydride → HCID 66753134, compound

HRID 1642403Notes

Reaction equation

HRID 1642403 reaction equation
[Cl:1][C:2]1[S:28][C:5]2=[N:6][C:7](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=3[O:22][CH2:23][C:24](C)([CH3:26])[CH3:25])=[C:8](I)[C:9](=[O:10])[N:4]2[CH:3]=1.[H-].[Na+].C(OC1C(OC)=CC=CC=1C=O)C(C)C.C1(COC2C(OC)=CC=CC=2/C=C/C2N=C3SC=CN3C(=O)C=2I)CC1>CS(C)=O>[Cl:1][C:2]1[S:28][C:5]2=[N:6][C:7](/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=3[O:22][CH2:23][CH:24]([CH3:25])[CH3:26])=[CH:8][C:9](=[O:10])[N:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 137497933-Methoxy-2-(2-methylpropoxy)benzaldehydeHCID 66753261HCID 66753261, compoundHCID 66753592HCID 66753592, compound

Product 1

HCID 66753134HCID 66753134, compoundYield 583.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Step 2 intermediate from Intermediate 19 (1.2 g, 2.412 mmol) was reacted with NaH (60% dispersion in mineral oil, 105 mg, 2.610) and 2-isobutoxy-3-methoxybenzaldehyde (546 mg, 2.412 mmol) in dry DMSO (10 ml) according to the procedure outlined in Intermediate 2, Step 3 to yield 5.5 g of the desired compound as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.03 (d, J=6.6 Hz, 6H), 1.98-2.06 (m, 1H), 3.68 (d, J=6.6 Hz, 2H), 3.79 (s, 3H), 6.30 (s, 1H), 6.98-7.16 (m, 3H), 7.30-7.33 (m, 1H), 8.05 (d, J=16.2 Hz, 1H), 8.23 (s, 1H).

Sources & evidence

ORD record
ord-884c408516a5421fa667e53bf48f38e3
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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