Cumylamine → HCID 178456997, compound

HRID 2268743Notes

Reaction equation

HRID 2268743 reaction equation
Cl[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([Cl:11])[S:10][C:5]=2[S:4](=[O:13])(=[O:12])[N:3]=1.[C:14]([NH2:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:16])[CH3:15]>C(O)C>[Cl:11][C:9]1[S:10][C:5]2[S:4](=[O:13])(=[O:12])[N:3]=[C:2]([NH:23][C:14]([CH3:16])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:15])[NH:7][C:6]=2[CH:8]=1

Participants

4

Reactant 2

HCID 68509CumylamineHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178456997HCID 178456997, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (1.0 g, 3.9 mmol) and cumylamine (1.06 g, 7.8 mmol) in ethanol (6 ml) was stirred for 31 h at 120° C. in a sealed flask. The cooled solution was concentrated in vacuo and the residue dissolved in 1N sodium hydroxide (50 ml) followed by treatment with decolourising charcoal. After filtration, the clear solution was acidified to pH <2 with 4M hydrochloric acid and the precipitate was filtered off and recrystallised from ethanol to give 278 mg (20%) of the title compound; mp ca. 360° C. (decomposes gradually above 200° C.); 1H-NMR (DMSO-d6): δ1.68 (s, 6H), 7.12 (s, 1H), 7.17-7.41 (m, 6H), 10.72 (br s, 1H); MS: m/e 355/357 (M+); (C14H14ClN3O2S2) calc C, 47,25; H, 3.97; N, 11.81; found C, 46.82; H, 3.96; N, 11.62.

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. dissolutionthe residue dissolved in 1N sodium hydroxide (50 ml)
  3. filtrationAfter filtration
  4. filtrationthe precipitate was filtered off
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-59a66180165d4fde8c70363e11832e52
Source dataset
uspto-grants-2001_12
Patent number
US06329367B1

Reaction notes

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