Water → HCID 86616751, compound

HRID 1726841Notes

Reaction equation

HRID 1726841 reaction equation
[OH:1][N:2]=[C:3]1[CH:7]=[CH:6][S:5][C:4]1=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:9]#[N:10].[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C.O>O1CCCC1.ClCCl>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([S:35]([O:1][N:2]=[C:3]3[CH:7]=[CH:6][S:5][C:4]3=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH3:17])[C:9]#[N:10])(=[O:37])=[O:36])=[CH:31][CH:30]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 223528924-(Chlorosulfonyl)phenyl 4-methylbenzene-1-sulfonateHCID 86616752HCID 86616752, compound

Product 1

HCID 86616751HCID 86616751, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 490 g of tetrahydrofuran were dissolved 45 g (0.19 mol) of (3-(hydroxy)imino-3H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile in Synthesis Example 14 and 61.8 g (0.19 mol) of 4-(4′-methylphenylsulfonyloxy)benzenesulfonyl chloride in Synthesis Example 7. To the solution cooled, 20.6 g (0.20 mol) of triethylamine was added dropwise such that the temperature might not exceed 10° C. The solution was allowed to ripen for 1 hour at room temperature, after which 150 g of water and 500 g of dichloromethane were added. The organic layer was separated, and washed with 150 g of water three times. The organic layer was concentrated in vacuum to 130 g. Methanol was added to the concentrate for recrystallization, followed by filtration and drying. There was obtained 83 g of yellow crystals. The crystals were purified by silica gel column chromatography (eluent, dichloromethane). The elute was concentrated, followed by recrystallization from methanol, filtration and drying. There was obtained 77 g of yellow crystals (yield 72%).

Workup

  1. customin Synthesis Example 7
  2. temperatureTo the solution cooled
  3. customexceed 10° C
  4. customThe organic layer was separated
  5. washwashed with 150 g of water three times
  6. concentrationThe organic layer was concentrated in vacuum to 130 g
  7. additionMethanol was added to the
  8. concentrationconcentrate for recrystallization
  9. filtrationfollowed by filtration
  10. customdrying

Sources & evidence

ORD record
ord-46c1ada5b3fe496da276ea9203232a02
Source dataset
uspto-grants-2009_02
Patent number
US07494760B2

Reaction notes

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