Tert-Butylamine → N-tert-Butyl-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxamide

HRID 1411986Notes

Reaction equation

HRID 1411986 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:12][C:5]2[S:6][C:7]([C:9]([OH:11])=O)=[CH:8][C:4]=2[CH2:3]1.[CH3:14][C:15]([NH2:18])([CH3:17])[CH3:16].C(N(CC)CC)C>O=S(Cl)Cl.ClCCl>[C:15]([NH:18][C:9]([C:7]1[S:6][C:5]2[CH2:12][C:2]([CH3:1])([CH3:13])[CH2:3][C:4]=2[CH:8]=1)=[O:11])([CH3:17])([CH3:16])[CH3:14]

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 580439285,5-dimethyl-4H,5H,6H-cyclopenta[b]thiophene-2-carboxylic acid

Product 1

HCID 86683779N-tert-Butyl-5,5-dimethyl-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxamideYield 97.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 282d (12.0 g, 61.0 mmol) in SOCl2 (80 mL) was heated at 65° C. for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with dichloromethane (20 mL), which was added to the solution of 2-methylpropan-2-amine (4.45 g, 61.0 mmol) and triethylamine (18.0 g, 180 mmol) in dichloromethane (180 mL). The resulting mixture was stirred for 16 h and diluted with dichloromethane (200 mL). It was washed with water (3×50 mL), dried over anhydrous Mg2SO4, filtered, and evaporated under reduced pressure to afford 282e (15.0 g, 97%) as yellow solid. MS-ESI: [M+H]+ 252.0

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with dichloromethane (20 mL), which
  3. washIt was washed with water (3×50 mL)
  4. dry with materialdried over anhydrous Mg2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6a0a2392fa624de38328ee578d524167
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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