Trifluoroacetic acid → HCID 85957959, compound

HRID 2382518Notes

Reaction equation

HRID 2382518 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:36])[C:14]1[CH:19]=[CH:18][C:17]([N:20]=[N:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][SH:35])=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)(C)(C)C>>[SH:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([N:21]=[N:20][C:17]2[CH:16]=[CH:15][C:14]([C:13]([OH:36])=[O:12])=[CH:19][CH:18]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86612899HCID 86612899, compound

Product 1

HCID 85957959HCID 85957959, compoundYield 90%

Procedure

An excess of trifluoroacetic acid (99%, Acros) was added to 0.2 g of 4-[4-(6-mercapto-hexyloxy)-phenylazo]-benzoic acid t-butyl ester. The mixture was stirred for 5 minutes to dissolve. Excess trifluoroacetic acid was flushed from the vessel using a stream of argon. Acetone was added to the crude mixture to remove unreacted starting materials. The deprotected product acid was solidified by acetone and filtered out. The solid product (compound 2, FIG. 11) was further purified by washing with several portions of acetone. The yield was 90-95%, and product characteristics were: 1H NMR (DMSO-d6) δ 13.08 (broad, 1H), 8.10 (d, J=9 Hz, 2H) 7.89 (dd, J=9 Hz, 4H), 7.11 (d, J=9 Hz, 2H), 4.06 (t, J=6 Hz, 2H), 2.7 (m, 2H), 1.78-1.25 (m, 9H). HR-MS (M+1) gave a mass of 359.1441 compared to the theoretical value of 359.1429 for C19H23O3N2S.

Workup

  1. dissolutionto dissolve
  2. customExcess trifluoroacetic acid was flushed from the vessel
  3. additionAcetone was added to the crude mixture
  4. customto remove unreacted
  5. filtrationfiltered out
  6. customThe solid product (compound 2, FIG. 11) was further purified
  7. washby washing with several portions of acetone
  8. customHR-MS (M+1) gave a mass of 359.1441

Sources & evidence

ORD record
ord-0ce27a7e45af41008fde7a56581ea46f
Source dataset
uspto-grants-2012_09
Patent number
US08263192B2

Reaction notes

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