Triethanolamine → HCID 178506208, compound

HRID 390759Notes

Reaction equation

HRID 390759 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:3]=1[CH2:4][N:5]([CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([C:19]([F:22])([F:21])[F:20])[CH:10]=1)[C:6]#[N:7].N(CCO)(CCO)CCO.C[Si]([N:45]=[N+:46]=[N-:47])(C)C>[OH-].[Na+]>[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][C:3]=1[CH2:4][N:5]([CH2:8][C:9]1[CH:10]=[C:11]([C:19]([F:20])([F:21])[F:22])[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:6]1[NH:47][N:46]=[N:45][N:7]=1

Participants

5

Reactant 3

HCID 7618TriethanolamineHCID 78378AzidotrimethylsilaneHCID 86614965(2-Chloro-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)benzyl)cyanamide

Product 1

HCID 178506208HCID 178506208, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5 gm of the compound from Step C, 50 mL of 2-methyl THF 5 mL, triethanolamine and 2.5 mL of trimethyl silyl azide was heated at 50° C. until reaction completion. When the reaction was judged complete, the reaction mixture was cooled and 50 mL of 1 N sodium hydroxide added. The layers were separated and the organic layer washed with 50 mL of 10% citric acid. The organic layer was concentrated and triturated with hexane to yield 4.6 of the desired compound. 85% yield. 1H NMR (400 MHz, CDCl3) 7.84 (s, 2H), 7.74 (m, 3H), 4.90 (s, 4H)C, H, N, Calculated, (found) 42.92 (42.98), 2.20 (1.97), 13.90 (13.54)

Workup

  1. temperaturethe reaction mixture was cooled
  2. customThe layers were separated
  3. washthe organic layer washed with 50 mL of 10% citric acid
  4. concentrationThe organic layer was concentrated
  5. customtriturated with hexane

Sources & evidence

ORD record
ord-5d403dbdb4c24f4aa5c8d719f2a811a7
Source dataset
uspto-grants-2013_02
Patent number
US08383660B2

Reaction notes

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