Tert-Butylamine → HCID 178448912, compound

HRID 2268736Notes

Reaction equation

HRID 2268736 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]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>>[C:14]([NH:18][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)([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 6385Tert-ButylamineHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178448912HCID 178448912, compoundYield 52%

Procedure

A solution of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (5.0 g, 19.45 mmol) in tert-butylamine (20 ml, 0.19 mol) was stirred for 20 h at 125° C. in a sealed flask. The cooled solution was concentrated in vacuo and the residue was stirred with water (25 ml) followed by adjustment to pH 2 with 4M hydrochloric acid. The resulting precipitate was isolated by filtration, washed with water, and then redissolved in 1 N sodium hydroxide (130 ml) followed by treatment with decolorising charcoal. After filtration, the clear solution was acidified to pH 2 and the precipitate was filtered off and recrystallised from methanol to give 2.91 g (52%) of the pure title compound; mp 368-372° C.; 1H-NMR (DMSO-d6): δ1.37 (s, 9H), 6.79 (br s, 1H), 7.11 (s, 1H), 10.55 (br s, 1H); MS: m/e 293/295 (M+); (C9H12N3Cl1O2S2) calc. C, 36.79; H, 4.12; N, 14.30; Cl, 12.07; S, 21.83; found C, 36.90; H, 4.11; N, 14.18; Cl, 12.05; S, 21.89.

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water
  4. dissolutionredissolved in 1 N sodium hydroxide (130 ml)
  5. filtrationAfter filtration
  6. filtrationthe precipitate was filtered off
  7. customrecrystallised from methanol

Sources & evidence

ORD record
ord-3cfbd7c3317549b7bb41bcbc6d777b5a
Source dataset
uspto-grants-2001_12
Patent number
US06329367B1

Reaction notes

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