Triethylamine → HCID 22277799, compound

HRID 2055306Notes

Reaction equation

HRID 2055306 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([C:22]([NH:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1)=[O:27])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 2984422-Dibenzothiophenamine

Product 1

HCID 22277799HCID 22277799, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Aminodibenzthiophene (Bull. Soc. Chim. Fr. (1996), 133 (6), 597-610; 2.0 g, 10 mmol) and triethylamine (1.11 g, 11 mmol) were dissolved in DCM (50 ml) and cooled in an ice bath. A solution of pivaloyl chloride (1.21 g, 10 mmol) in DCM (10 ml) was added slowly and the resultant solution was stirred at ambient temperature for 16 hours then evaporated in vacuo. The residue was triturated with methanol to leave the product as a colourless solid (1.85 g). NMR: 9.40 (s, 1H), 8.59 (s, 1H), 8.17 (m, 1H), 7.98 (d, 1H), 7.90 (d, 1H), 7.73 (dd, 1H), 7.46 (m, 2H), 1.15 (s, 9H); m/z 284.

Workup

  1. temperaturecooled in an ice bath
  2. customthen evaporated in vacuo
  3. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-f2b9353897e44d4dbe4fb5856237a6b6
Source dataset
uspto-grants-2008_02
Patent number
US07332492B2

Reaction notes

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