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

HRID 1665949Notes

Reaction equation

HRID 1665949 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-1598ce1ad82448e69e128f2e40900dac
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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