Dimethylamine → HCID 59262908, compound

HRID 2383419Notes

Reaction equation

HRID 2383419 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH:9]([CH:12]=O)[CH2:8][CH2:7][C:5]=2[N:6]=1.[CH3:14][NH:15][CH3:16]>C1(C)C=CC=CC=1.C(OCC)C.C1COCC1>[CH3:14][N:15](/[CH:12]=[C:9]1\[C:10](=[O:11])[C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH2:7][CH2:8]\1)[CH3:16]

Participants

6

Reactant 2

HCID 674DimethylamineHCID 248876322-Methyl-7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazole-6-carbaldehyde

Product 1

HCID 59262908HCID 59262908, compoundYield 87.9%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-methyl-7-oxo-4,5,6,7-tetrahydrobenzo[d]thiazole-6-carbaldehyde (5 g, 25.6 mmol) in toluene (50 mL) and diethylether (25 mL) was added dimethylamine (15 mL, 35 mmol) as a solution in THF. The reaction was stirred for at room temperature for 40 hours. The reaction was then concentrated under reduced pressure to give a brown residue, which was triturated with hexane to give the desired product (5.0 g, 87%) as a solid. 1H NMR (DMSO-d6, 400 MHz): δ 7.35 (s, 1H), 3.10 (s, 6H), 2.98 (t, J=6.2 Hz, 2H), 2.82 (t, J=6.2 Hz, 2H), 2.65 (s, 3H); LCMS [M+H]: 223.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. customto give a brown residue, which
  3. customwas triturated with hexane

Sources & evidence

ORD record
ord-441fa06513bc43eb9be9332ce00f23b8
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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