Ammonia → HCID 54472013, compound

HRID 650593Notes

Reaction equation

HRID 650593 reaction equation
C[N:2]1CCOCC1.[CH:8](=[C:12]1[C:21]2[CH:20]=[C:19]([C:22]([OH:24])=O)[S:18][C:17]=2[CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:9][CH2:10][CH3:11].ClC(OCC(C)C)=O.N>CCOC(C)=O.O.C1COCC1>[CH:8](=[C:12]1[C:21]2[CH:20]=[C:19]([C:22]([NH2:2])=[O:24])[S:18][C:17]=2[CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:9][CH2:10][CH3:11]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 53851345HCID 53851345, compound

Product 1

HCID 54472013HCID 54472013, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Methylmorpholine (0.69 ml) was added to a mixture of 4-n-butylidene-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2-carboxylic acid (1.05 g) and THF (10 ml) at −15˜−20° C. under nitrogen atmosphere, and isobutyl chloroformate (0.82 ml) was added thereto over 2 minutes. The mixture was stirred under the same condition for 30 minutes, and conc. ammonia (c.NH3) was added thereto. The mixture was stirred at r.t. for 2 hours. The reaction mixture was poured into a mixture of water and AcOEt to precipitate. The precipitate was collected by filtration, washed with water and Et20, and dried in vacuo to give 4-n-butylidene-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-2-carboxamide (0.59 g).

Workup

  1. stirringThe mixture was stirred at r.t. for 2 hours
  2. customto precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water and Et20
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2b5a9d077b094d71b659a1c7d68d8825
Source dataset
uspto-grants-2001_08
Patent number
US06274619B1

Reaction notes

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