Sodium hydride → HCID 86232840, compound

HRID 554321Notes

Reaction equation

[C:1]1([C:7]2[NH:11][CH:10]=[C:9]([CH:12]=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[S:31]1[C:35]2[CH:36]=[C:37]([S:40](Cl)(=[O:42])=[O:41])[CH:38]=[CH:39][C:34]=2[N:33]=[CH:32]1>>[S:31]1[C:35]2[CH:36]=[C:37]([S:40]([N:11]3[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:8][C:9]([CH:12]=[O:13])=[CH:10]3)(=[O:41])=[O:42])[CH:38]=[CH:39][C:34]=2[N:33]=[CH:32]1

Participants

Reactant 4

HCID 24758Sodium hydride

HCID 3633615-Crown-5

HCID 27951701,3-Benzothiazole-6-sulfonyl chloride

HCID 110520905-Phenyl-1H-pyrrole-3-carboxaldehyde

Product 1

HCID 86232840HCID 86232840, compoundYield 85.4%

Procedure

Using 5-phenyl-1H-pyrrole-3-carbaldehyde (135 mg), sodium hydride (60% in oil, 38.3 mg), 15-crown-5 (0.18 mL) and 6-benzothiazolesulfonyl chloride (206 mg), a procedure as in Reference Example 219 was performed to give the title compound as white crystal (yield 248 mg, 85%).

Sources & evidence

ORD record: ord-09c66b30e0f745f0bdcc8198a5dc1a1e
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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