Dimethylformamide dimethyl acetal → N'-{6-[1-Dimethylamino-meth-(E)-ylidene]-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl}-N,N-dimethyl-formamidine

HRID 1807645Notes

Reaction equation

HRID 1807645 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.CO[CH:14]([N:17]([CH3:19])[CH3:18])OC>>[CH3:14][N:17]([CH3:19])/[CH:18]=[C:9]1/[C:10](=[O:11])[C:4]2[S:3][C:2]([N:1]=[CH:14][N:17]([CH3:19])[CH3:18])=[N:6][C:5]=2[CH2:7][CH2:8]/1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 5878502-Amino-4,5,6,7-tetrahydro-1,3-benzothiazol-7-one

Product 1

HCID 66900576N'-{6-[1-Dimethylamino-meth-(E)-ylidene]-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl}-N,N-dimethyl-formamidine

Conditions

Temperature
100 °C

Procedure

A suspension of 2-amino-5,6-dihydro-4H-benzothiazol-7-one (3.5 g, 20.81 mmol) in dimethoxymethyldimethylamine (12 mL, 90 mmol) was heated at 100° C. with stirring for 65 h. The RM was then evaporated to dryness in vacuo and the residue was suspended in EtOAc. After 1 h at 4° C., the solid was filtered off, washed with EtOAc and then dried under high vacuum at 60° C. to give the pure title product as brown crystals. LC: tR 3.25 min (method D). MS: M+H=279. 1H-NMR in DMSO-d6: 8.40 (s, 1H); 7.23 (s, 1H); 3.15 (s, 3H); 3.05 (s, 6H); 2.97 (s, 3H); 2.91 (t, 2H); 2.67 (t, 2H).

Workup

  1. customThe RM was then evaporated to dryness in vacuo
  2. waitAfter 1 h at 4° C.
  3. filtrationthe solid was filtered off
  4. washwashed with EtOAc
  5. customdried under high vacuum at 60° C.

Sources & evidence

ORD record
ord-3ce51f2c345045de8d2b1780af622995
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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