1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(1,2,4-Triazol-1-ylmethylcarbonylamino)dibenzothiophene

HRID 2055307

Reaction equation

HRID 2055307 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.[N:15]1([CH2:20][C:21](O)=[O:22])[CH:19]=[N:18][CH:17]=[N:16]1.O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C>O.CN(C=O)C>[N:15]1([CH2:20][C:21]([NH:1][C:2]2[CH:14]=[CH:13][C:5]3[S:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:4]=3[CH:3]=2)=[O:22])[CH:19]=[N:18][CH:17]=[N:16]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2984422-DibenzothiophenamineHCID 18101801,2,4-Triazole-1-acetic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 222777952-(1,2,4-Triazol-1-ylmethylcarbonylamino)dibenzothiopheneYield 84.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Aminodibenzthiophene (Bull. Soc. Chim. Fr. (1996), 133 (6), 597-610; 500 mg, 2.5 mmol) was dissolved DMF (10 ml) and 2-(1,2,4-triazol-1-yl)acetic acid (318 mg, 2.5 mmol) was added in one portion followed by 1-hydroxybenztriazole hydrate (383 mg, 5.0 mmol) and EDAC (960 mg, 5.0 mmol). The resultant mixture was stirred for 16 hours at ambient temperature then poured on to water (100 ml). A fine white solid was collected which was washed extensively with water, methanol (25 ml) and ether (25 ml) to leave a colourless solid (650 mg). NMR: 10.62 (brs, 1H), 8.18 (m, 2H), 8.16 (m, 1H), 7.99 (m, 3H), 7.62 (dd, 1H), 7.50 (m, 2H), 5.20 (s, 2H); m/z 309.

Workup

  1. additionwas added in one portion
  2. customA fine white solid was collected which
  3. washwas washed extensively with water, methanol (25 ml) and ether (25 ml)

Sources & evidence

ORD record
ord-a098e2fdce274a7baab1a948b7ae8e35
Source dataset
uspto-grants-2008_02
Patent number
US07332492B2

Linked notes

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