Trichloroacetyl isocyanate → HCID 69627417, compound

HRID 1281444Notes

Reaction equation

HRID 1281444 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:38])[C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[C:20]([O:33][CH2:34][CH2:35][OH:36])=[C:19]([Br:37])[CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(Cl)(Cl)[C:41]([N:43]=C=O)=[O:42]>C(Cl)Cl>[Br:37][C:19]1[C:20]([O:33][CH2:34][CH2:35][O:36][C:41](=[O:42])[NH2:43])=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=2)[CH:22]=[C:17]([C:16](=[O:38])[NH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 22237557HCID 22237557, compound

Product 1

HCID 69627417HCID 69627417, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(8-phenyl-octyl)-3-bromo-5-(m-trifluoromethylphenyl)-4-(2-hydroxyethoxy)-benzamide (0.463 g, 0.78 mmol, 1 eq) in CH2Cl2 (10 mL) was added trichloroacetyl isocyanate (0.100 mL, 0.84 mmol, 1.1 eq) The reaction was stirred at rt 15 minutes and oven-dried alumina was added. The reaction was stirred overnight at rt and concentrated in vacuo. The residue was purified by flash chromatography (30 to 60% EtOAc:hexane) to afford the title compound (0.308 g, 62%) as a oil. 1H NMR (DMSO-d6) δ 8.56 (bt, 1H); 8.13 (d, 1H); 7.89 (m, 3H); 7.72 (dd, 1H); 7.24 (m, 2H); 7.14 (m, 3H); 6.40 (bs, 2H); 3.90 (dd, 2H); 3.70 (dd, 2H); 3.23 (dd, 2H); 2.52 (t, 2H); 1.25 (m, 4H); 1.27 (m, 8H); IR (KBr) 3330, 2920, 2850, 1720, 1640, 1600, 1550, 1460, 1410, 1330, 1180, 1120 cm−1; mass spectrum [(+)ESI], m/z 635/637 (M+H)+; Anal. Calcd. for C31H34BrF3N2O4: C, 58.59; H, 5.39; N, 4.41, Found: C, 57.26; H, 5.46; N, 4.38.

Workup

  1. additionoven-dried alumina was added
  2. stirringThe reaction was stirred overnight at rt
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (30 to 60% EtOAc:hexane)

Sources & evidence

ORD record
ord-70da6d4eb1024ef7ac45bfedb096c7af
Source dataset
uspto-grants-2002_09
Patent number
US06451827B2

Reaction notes

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