(+)-Epichlorohydrin → HCID 67131052, compound

HRID 527952Notes

Reaction equation

HRID 527952 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.[CH2:13]([C@H:15]1[O:17][CH2:16]1)[Cl:14]>CC#N>[Cl:14][CH2:13][C@@H:15]([OH:17])[CH2:16][NH:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1

Participants

4

Reactant 2

HCID 149428(+)-EpichlorohydrinHCID 6869016-amino-3,4-dihydro-2H-1,4-benzothiazin-3-one

Product 1

HCID 67131052HCID 67131052, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

A suspension of 6-amino-4H-benzo[1,4]thiazin-3-one (18.0 g, 100 mmol; commercial) and Ca(OTf)2 (0.5 eq.) in MeCN (800 mL) was heated at 50° for 1 h. (S)-epichlorohydrin (18.5 g, 200 mmol) was added and the mixture was stirred at rt for 72 h and at 45° C. for 24 h. The volatiles were removed under reduced pressure. After aqueous workup and extraction with EA, the title intermediate crystallised from EA to afford a beige solid (17.38 g, 64% yield).

Workup

  1. additionwas added
  2. customThe volatiles were removed under reduced pressure
  3. extractionAfter aqueous workup and extraction with EA
  4. customthe title intermediate crystallised from EA

Sources & evidence

ORD record
ord-edc9d0635b3e480b90fecb7df3add9dc
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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