Triethanolamine → HCID 178506208, compound

HRID 2075119Notes

Reaction equation

HRID 2075119 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-499a530ea3b64abe8a62d4e497961329
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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