Ammonia → tert-Butyl (5-bromo-2-carbamoylthiophen-3-yl)carbamate

HRID 11424

Reaction equation

HRID 11424 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7](O)=[O:8])=[C:4]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]=1.OC1C2N=N[NH:24]C=2C=CC=1.Cl.CN(C)CCCN=C=NCC.N>C(#N)C>[Br:1][C:2]1[S:6][C:5]([C:7]([NH2:24])=[O:8])=[C:4]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219758545-Bromo-3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 21975856tert-Butyl (5-bromo-2-carbamoylthiophen-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Bromo-3-[(t-butyloxycarbonyl)amino]thiophene-2-carboxylic acid (0.80 g) was stirred in acetonitrile (80 ml). Hydroxybenztriazole (1.41 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.62 g) were added and stirring continued at room temperature for 10 minutes. Concentrated aqueous ammonia solution (8 ml) was added and the reaction mixture was heated to reflux for 1 h. The acetonitrile was removed by evaporation. Water (100 ml) was added and the mixture was sonicated and triturated. The resultant off-white solid was then collected by filtration, washed with water and dried under vacuum (0.763 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. customThe acetonitrile was removed by evaporation
  4. additionWater (100 ml) was added
  5. customthe mixture was sonicated
  6. customtriturated
  7. filtrationThe resultant off-white solid was then collected by filtration
  8. washwashed with water
  9. customdried under vacuum (0.763 g)

Sources & evidence

ORD record
ord-0290ac04ad0e445e81e62a6c3df508c9
Source dataset
uspto-grants-2006_08
Patent number
US07098240B2

Linked notes

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