Methanamine, N-methoxy-, hydrochloride (1:1) → 4,5,6,7-tetrahydro-N-methoxy-N,5,5-trimethyl-benzo[c]thiophene-1-carboxamide

HRID 2240812Notes

Reaction equation

HRID 2240812 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:13][CH2:12][C:5]2=[C:6]([C:9](O)=[O:10])[S:7][CH:8]=[C:4]2[CH2:3]1.Cl.[CH3:16][NH:17][O:18][CH3:19].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CS(C)=O>[CH3:19][O:18][N:17]([CH3:16])[C:9]([C:6]1[S:7][CH:8]=[C:4]2[CH2:3][C:2]([CH3:14])([CH3:1])[CH2:13][CH2:12][C:5]=12)=[O:10]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57508882HCID 57508882, compound

Product 1

HCID 598608664,5,6,7-tetrahydro-N-methoxy-N,5,5-trimethyl-benzo[c]thiophene-1-carboxamideYield 95.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid (20 g, 95 mmol) in DMSO (150 mL) is added N,O-dimethylhydroxylamine hydrochloride (12.06 g, 124 mmol) and DIPEA (65 mL, 380 mmol), followed by TBTU (33.59 g, 105 mmol, dissolved in DMF (70 mL)). The reaction mixture is stirred at rt for 2 h before it is poured into water/ice and extracted twice with diethyl ether (2×100 mL). The organic extracts are washed with sat. aq. NaHCO3 solution, 10% aq. citric acid solution and brine, dried over Na2SO4, filtered, evaporated and dried to give 5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophene-1-carboxylic acid methoxy-methyl-amide (23 g) as a brown oil; LC-MS: tR=1.01 min, [M+1]=254.14.

Workup

  1. extractionextracted twice with diethyl ether (2×100 mL)
  2. washThe organic extracts are washed with sat. aq. NaHCO3 solution, 10% aq. citric acid solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried

Sources & evidence

ORD record
ord-ec8d1a64d6cb43b3ba1c946c5e1a1447
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

Loading…