Methanol → HCID 22671955, compound

HRID 1279610Notes

Reaction equation

HRID 1279610 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2N)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=1.[C:32]([BH3-])#[N:33].[Na+].[CH3:36][OH:37]>C(O)(=O)C>[C:1]1([S:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2[NH:33][CH2:32][C:23]2[CH:24]=[CH:25][C:26]([C:27]([O:37][CH3:36])=[O:28])=[CH:29][CH:30]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 12173TerephthalaldehydeHCID 5003444Sodium cyanoborohydrideHCID 16773163HCID 16773163, compound

Product 1

HCID 22671955HCID 22671955, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-phenylsulfonylamino-3-aminobenzotrifluoride (100 mg; prepared in Reference Example 26.) and terephthal aldehyde acid methyl ester (78 mg) in MeOH (2 ml), acetic Acid (1.5 ml) was added. The mixture was stirred for 2 hours at room temperature. After stirring, a solution of sodium cyanoborohydride (30 mg) in MeOH (2 ml) was added. The mixture was stirred for 2 hours at room temperature. The reaction solution was extracted with H2O-AcOEt, washed, dried over, filtered and concentrated. The precipitate was washed with hexane to give the title compound (146 mg) having the following physical data.

Workup

  1. stirringAfter stirring
  2. stirringThe mixture was stirred for 2 hours at room temperature
  3. extractionThe reaction solution was extracted with H2O-AcOEt
  4. washwashed
  5. customdried over,
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe precipitate was washed with hexane

Sources & evidence

ORD record
ord-cf5f60eb12044e5a91718a1c4c630019
Source dataset
uspto-grants-2002_09
Patent number
US06448290B1

Reaction notes

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