Hydrochloric Acid → HCID 22237691, compound

HRID 1884678Notes

Reaction equation

HRID 1884678 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[C:17]=2[OH:18])[C:12](O)=[O:13])[CH:6]=[CH:7][CH:8]=1.[CH2:31]([O:38][C:39]1[CH:53]=[CH:52][C:42]([CH2:43][O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][NH2:51])=[CH:41][CH:40]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(CC)CC)C.Cl>O=S(Cl)Cl.C(Cl)Cl>[CH2:31]([O:38][C:39]1[CH:40]=[CH:41][C:42]([CH2:43][O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][NH:51][C:12](=[O:13])[C:11]2[CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:27])([F:28])[F:26])[CH:20]=3)[C:17]([OH:18])=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:29])[F:30])[CH:4]=3)[CH:10]=2)=[CH:52][CH:53]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 22237421HCID 22237421, compoundHCID 22237463HCID 22237463, compound

Product 1

HCID 22237691HCID 22237691, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A stirring solution of 3,5-bis-(m-trifluoromethylphenyl)-4-hydroxybenzoic acid (0.800 g, 1.87 mmol) in SOCl2 (10 mL) was heated at reflux for 1.5 h, then cooled and concentrated in vacuo. The acid chloride was dried in vacuo overnight. The acid chloride was dissolved in CH2Cl2 (10 mL) and added to a solution of 6-(4-benzyloxy-benzyloxy)hexylamine (0.765 g, 2.44 mmol) and triethylamine (0.92 mL, 6.54 mmol) in CH2Cl2 (10 mL) at 0° C. After stirring for 4 h at 0° C., 1.0 N HCl was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4), and concentrated to give 1.15 g (85%) of the amide as an oil: 1H NMR (DMSO-d6) δ 9.30 (s, 1H), 8.44 (t, 1H), 7.94-7.70 (m, 10H), 7.41 (m, 4H), 7.20 (d, 2H), 6.95 (d, 2H), 5.08 (s, 2H), 4.35 (s, 2H), 3.42-3.20 (m, 4H), 1.50 (m, 4H), 1.32 (m, 4H).

Workup

  1. temperatureat reflux for 1.5 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. dry with materialThe acid chloride was dried in vacuo overnight
  5. dissolutionThe acid chloride was dissolved in CH2Cl2 (10 mL)
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic phase was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f87f35dd1bfe4050b05d05c571fe10e5
Source dataset
uspto-grants-2004_07
Patent number
US06765021B2

Reaction notes

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