p-Toluenesulfonic acid → HCID 178522900, compound

HRID 2289957Notes

Reaction equation

HRID 2289957 reaction equation
[NH2:1][C:2](=[S:26])[C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([F:13])[CH:12]=1)[N:9]=[CH:8][C:7]([C:14]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[O:15])=[C:6]2[OH:25].[C:27]1(C)C=CC(S(O)(=O)=O)=C[CH:28]=1.C(OC(OCC)CBr)C>C(O)(=O)C.C(OCC)(=O)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][NH:16][C:14]([C:7]2[CH:8]=[N:9][C:10]3[C:5]([C:6]=2[OH:25])=[CH:4][C:3]([C:2]2[S:26][CH:27]=[CH:28][N:1]=2)=[CH:12][C:11]=3[F:13])=[O:15])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 178514136HCID 178514136, compound

Product 1

HCID 178522900HCID 178522900, compoundYield 544.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of the title compound of Example 52 (0.14 g) and p-toluenesulfonic acid (0.0084 g) in 2 mL acetic acid is added bromoacetaldehyde diethyl acetal (0.08 mL). The reaction is heated at 100° C. for approximately 45 minutes. The reaction is cooled to room temperature and diluted with 30 mL ethyl acetate. The solid is filtered and dried to give the desired product (0.11 g).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. filtrationThe solid is filtered
  3. customdried

Sources & evidence

ORD record
ord-709e3ffad828433a92aa5f1ac4cc2745
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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