Ammonia → HCID 70023713, compound

HRID 1369290Notes

Reaction equation

HRID 1369290 reaction equation
[CH:1]1[C:6]2[S:7][CH2:8][CH2:9]CO[C:5]=2[C:4]([C:12]([OH:14])=O)=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH3:37].CN([CH:41]=[O:42])C>C(OCC)(=O)C>[CH:1]1[C:6]2[S:7][CH2:8][CH2:9][O:42][CH2:41][C:5]=2[C:4]([C:12]([NH2:37])=[O:14])=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18519016HCID 18519016, compound

Product 1

HCID 70023713HCID 70023713, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 7,8-dihydro-6H-5-oxa-9-thia-benzocycloheptene-4-carboxylic acid (16.5 g, 78.4 mmol) in 100 mL DMF was added in succession solid HOBT (213 g, 1573 mmol), solid EDC hydrochloride (30.1 g, 157.0 mmol), and 25% aqueous ammonia (18 ml, 128.4 mmol). After stirring for 48 h, the reaction mixture was diluted with 200 mL ethyl acetate and washed with water, 1N HCl, saturated NaHCO3, sated NH4Cl, and brine. Drying over Na2SO4 and concentration yielded the amide as a tan solid (10.5 g, 64%).

Workup

  1. washwashed with water, 1N HCl, saturated NaHCO3
  2. dry with materialDrying over Na2SO4 and concentration

Sources & evidence

ORD record
ord-87c1997810a541a6b16b3711eb1a888a
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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