Water → HCID 86743100, compound

HRID 1904228Notes

Reaction equation

HRID 1904228 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][S:6][CH2:5][CH:4]([C:9]([OH:11])=O)[NH:3]1.N[CH2:13][CH2:14][N:15]1[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]1[CH3:21].C1([N:28]=C=NC2CCCCC2)CCCCC1.O>CN(C)C=O.C(Cl)Cl>[CH3:21][C:16]1[N:15]([CH2:14][CH2:13][CH:5]2[CH:4]([C:9]([NH2:28])=[O:11])[NH:3][C:2](=[O:1])[CH2:8][CH2:7][S:6]2)[C:19]([CH3:20])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 137700502-(2,5-Dimethyl-1H-pyrrol-1-yl)ethan-1-amineHCID 14442188HCID 14442188, compound

Product 1

HCID 86743100HCID 86743100, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3.5 g (0.02 mol) of 5-oxoperhydro-1,4-thiazepine-3-carboxylic acid and 2.8 g (0.02 mol) of 1-(2-aminoethyl)-2,5-dimethylpyrrole are dissolved in 10 ml of dimethylformamide. After addition of 4.2 g (0.02 mol) of dicyclohexylcarbodiimide, dissolved in 10 ml of methylene chloride, to the mixture at 0° C., it is stirred at room temperature for 24 h, then water is added and the mixture is filtered with suction. The filtrate is extracted with methylene chloride, and the extract is chromatographed over a silica gel column using ethyl acetate as the mobile phase. Yield: 1.2 g (20% of theory), Melting point: 181°-183° C. Elemental analysis: C14H21N3O2S (295.41) calculated: C 56.9 H 7.2 N 14.2 0 10.8 S 10.9 found: C 57.4 H 6.9 N 13.8 0 11.2 S 10.8

Workup

  1. filtrationthe mixture is filtered with suction
  2. extractionThe filtrate is extracted with methylene chloride
  3. customthe extract is chromatographed over a silica gel column

Sources & evidence

ORD record
ord-e67be6904e4240b49954fbc0f1668b1a
Source dataset
uspto-grants-1989_06
Patent number
US04837225

Reaction notes

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