HCID 15549657, compound → HCID 9926129, compound

HRID 381246Notes

Reaction equation

HRID 381246 reaction equation
C([O:4][C:5](=[O:23])[NH:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[S:9][C:8]=1[C:19](O)([CH3:21])[CH3:20])C=C.CC([O-])(C)C.[K+]>C1COCC1>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[S:9][C:8]3[C:19]([CH3:20])([CH3:21])[O:23][C:5](=[O:4])[NH:6][C:7]=3[CH:11]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 15549657HCID 15549657, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 9926129HCID 9926129, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [5-(3-Chloro-phenyl)-2-(1-hydroxy-1-methyl-ethyl)-thiophen-3-yl]-carbamic acid allyl ester (0.12 g, 0.34 mmol) in anhydrous THF (5.0 mL) was added KOtBu (0.076 g, 0.068 mmol) and stirred for 15 minutes, quenched with H2O, and in situ crystallization was carried out by adding minimal amount of MeOH to the solution. The white crystals were collected on a Büchner funnel, mp 123-125° C. 1H NMR (DMSO-d6) δ1.64(s, 6H), 7.05(s, 1H), 7.37-7.48(m, 2H), 7.53-7.56(s, 1H) 7.67-7.68 (m,1H), 10.41(s, 1H); MS(EI) m/z 293/295(M+H); Anal. Calc. For C17H18ClNO3S: C, 57.24; H, 4.12; N, 4.77. Found: C, 56.93; H, 3.92; N, 4.97.

Workup

  1. customquenched with H2O
  2. customin situ crystallization
  3. additionby adding minimal amount of MeOH to the solution
  4. customThe white crystals were collected on a Büchner funnel, mp 123-125° C

Sources & evidence

ORD record
ord-930fe6e624ed47f2afd577ecf2240378
Source dataset
uspto-grants-2001_10
Patent number
US06306851B1

Reaction notes

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