Dimethylformamide → 8-Dimethylamino-methylene-6,8-dihydro-1-thia-3,6diaza-as-indacen-7one

HRID 2300267Notes

Reaction equation

HRID 2300267 reaction equation
[S:1]1[C:12]2[C:4](=[CH:5][CH:6]=[C:7]3[C:11]=2[CH2:10][C:9](=[O:13])[NH:8]3)[N:3]=[CH:2]1.C(O[CH:19](OC(C)(C)C)[N:20](C)[CH3:21])(C)(C)C.[CH3:28]N(C=O)C>CCOCC>[CH3:19][N:20]([CH3:21])[CH:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]3[C:12]=2[S:1](=[CH2:28])[CH:2]=[N:3]3)[NH:8][C:9]1=[O:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 111168276H-thiazolo[5,4-e]indol-7(8H)-one

Product 1

HCID 865855238-Dimethylamino-methylene-6,8-dihydro-1-thia-3,6diaza-as-indacen-7oneYield 77%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 1.0 g (5.3 mmol) of 6,8-dihydro-1-thia-3,6-diaza-as-indacen-7-one (Procedure B) in 7.5 mL of DMF was added 1.38 g (6.80 mmol) of N,N-dimethylformamide-di-t-butyl acetal. The mixture was stirred at ambient temperature for 1 h and diluted with 7.5 mL of Et2O. The resulting precipitate was isolated filtration to afford 8-dimethylamino-methylene-6,8-dihydro-1-thia-3,6-diaza-as-indacen-7-one as a tan solid (1.0 g, 77%): 1H NMR (DMSO-d6): δ3.33 (bs, 3H), 3.59 (bs, 3H), 6.97 (d, J=8.4, 1H), 7.33 (s, 1H), 7.62 (d, J=8.4, 1H), 9.13 (s,1H), 10.29 (s, 1H); APCI-MS: m/z 246 (M+H)+.

Workup

  1. customThe resulting precipitate was isolated
  2. filtrationfiltration

Sources & evidence

ORD record
ord-93bfd7e7f1c7403c88fc2d8402560e0e
Source dataset
uspto-grants-2002_12
Patent number
US06498176B1

Reaction notes

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