Ethanolamine → HCID 178527196, compound

HRID 1975933Notes

Reaction equation

HRID 1975933 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.[CH2:14]([CH2:16][NH2:17])[OH:15]>>[Cl:11][C:9]1[S:10][C:5]2[S:4](=[O:13])(=[O:12])[N:3]=[C:2]([NH:17][CH2:16][CH2:14][OH:15])[NH:7][C:6]=2[CH:8]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178527196HCID 178527196, compoundYield 60%

Conditions

Temperature
0 °C

Procedure

A solution of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (206 mg, 0.8 mmol) in ethanolamine (1.0 ml) was stirred for 18 h at 100° C. in a sealed flask. The cooled solution was concentrated in vacuo and the residue was stirred with water (5 ml) at 0° C. followed by adjustment to pH 2 with 4M hydrochloric acid. The product was isolated by filtration, washed with water, and recrystallised from ethanol/water to give 135 mg (60%) of the pure title compound; mp 260-261° C. dec.; 1H-NMR (DMSO-d6): δ3.26 (distorted q, 2H), 3.50 (t, 2H), 4.85 (br s, 1H), 7.07 (s, 1H), 7.20 (br s, 1H), 10.9 (br s, 1H); MS: m/e 281/283 (M+); (C7H8N3Cl1O3S2) calc C, 29.84; H, 2.86; N, 14.91; found C, 30.13; H, 2.84; N, 14.79.

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. customThe product was isolated by filtration
  3. washwashed with water
  4. customrecrystallised from ethanol/water

Sources & evidence

ORD record
ord-0bbceee0388140e18ce8340654d97088
Source dataset
uspto-grants-2001_05
Patent number
US06225310B1

Reaction notes

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