Triethylamine → HCID 15662240, compound

HRID 981462Notes

Reaction equation

HRID 981462 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:6]2[CH:16]=[C:17]([CH2:19][CH3:20])[S:18][C:5]=2[N:4]2[C:21]([CH2:24][CH2:25][CH3:26])=[N:22][N:23]=[C:3]12.C(N(CC)CC)C.[CH:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][C:35]=1[C:44](Cl)=[O:45]>C(Cl)(Cl)Cl>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]1[C:6]2[CH:16]=[C:17]([CH2:19][CH3:20])[S:18][C:5]=2[N:4]2[C:21]([CH2:24][CH2:25][CH3:26])=[N:22][N:23]=[C:3]2[CH:2]([NH:1][C:44]([C:35]2[CH:36]=[CH:37][C:38]3[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:34]=2)=[O:45])[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 15662239HCID 15662239, compound

Product 1

HCID 15662240HCID 15662240, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In 20 ml of chloroform was dissolved 1.5 g of 6-amino-4-(2-chlorophenyl)-2-ethyl-9-propyl-6H-thieno[3,2-f][1,2,4]-triazolo[4,3-a][1,4]diazepine, and 0.47 g of triethylamine was added to the solution. A solution of 0.89 g of naphthalene-2-carbonyl chloride in 10 ml of chloroform was added dropwise to the mixture at not more than 10° C. The mixture was further stirred for 1 hour at room temperature and washed with 0.1N hydrochloric acid, 0.1N sodium hydroxide and a saturated solution of sodium chloride in order. Thereafter, the solvent was distilled off under reduced pressure, and the residue was washed with diisopropyl ether. Ethanol was added to yield crystals, which were collected by filtration. The crystals were recrystallized from chloroform-ethanol to give 1.4 g of 4-(2-chlorophenyl)-2-ethyl-6-(2-naphthalenecarboxamido)-9-propyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine, m.p. 226°-227° C.

Workup

  1. additionwas added to the solution
  2. washwashed with 0.1N hydrochloric acid, 0.1N sodium hydroxide
  3. distillationThereafter, the solvent was distilled off under reduced pressure
  4. washthe residue was washed with diisopropyl ether
  5. additionEthanol was added
  6. customto yield crystals, which
  7. filtrationwere collected by filtration
  8. customThe crystals were recrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-2c5b056491a64fe4addaa88b449b4c5f
Source dataset
uspto-grants-1991_02
Patent number
US04992437

Reaction notes

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