Sodium hydride → HCID 73986464, compound

HRID 841897Notes

Reaction equation

HRID 841897 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH:18]=[C:19]1[S:23][C:22](=[O:24])[NH:21][C:20]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[S:33](Cl)(=[O:35])=[O:34]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:33]([C:29]1[S:28][CH:32]=[CH:31][CH:30]=1)(=[O:35])=[O:34])[CH:13]=[C:12]2[CH:18]=[C:19]1[S:23][C:22](=[O:24])[NH:21][C:20]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 855182-Thiophenesulfonyl chlorideHCID 178518467HCID 178518467, compound

Product 1

HCID 73986464HCID 73986464, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from step A (50 mg) was treated with 1.2 equivalents of NaH in DMF solution with cooling for 1 hr. 2-Thienylsulfonyl chloride (34 mg, 1.3 equivaltents) was added cautiously. After 18 hrs. at ambient temperature and finally at 70° C., the mixture was poured onto ice and the precipitate was filtered. The title compound was filtered and washed with ether. HPLC ‘System 1’ (Ex. 1) showed 80% purity; structure confirmed by mass spec [m\e 497 (M+1)].

Workup

  1. temperaturewith cooling for 1 hr
  2. additionat ambient temperature and finally at 70° C., the mixture was poured onto ice
  3. filtrationthe precipitate was filtered
  4. filtrationThe title compound was filtered
  5. washwashed with ether

Sources & evidence

ORD record
ord-db4595f340e647fa98ddaf8ba3cbd487
Source dataset
uspto-grants-2002_04
Patent number
US06372742B1

Reaction notes

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