Diketene → 5-Acetoacetylamino-6-fluoro-3-(2-propynyl)-2-benzothiazolinone

HRID 2253589Notes

Reaction equation

HRID 2253589 reaction equation
[NH2:1][C:2]1[C:3]([F:15])=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]#[CH:13])[C:6]=2[CH:14]=1.[CH2:16]=[C:17]1[O:21][C:19](=[O:20])[CH2:18]1.N1(C2C=CN=CC=2)CCCC1>C1C=CC=CC=1>[C:19]([NH:1][C:2]1[C:3]([F:15])=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]#[CH:13])[C:6]=2[CH:14]=1)(=[O:20])[CH2:18][C:17]([CH3:16])=[O:21]

Participants

5

Reactant 3

HCID 12661DiketeneHCID 755674-PyrrolidinopyridineHCID 139609955-Amino-6-fluoro-3-(prop-2-yn-1-yl)-1,3-benzothiazol-2(3H)-one

Product 1

HCID 197458095-Acetoacetylamino-6-fluoro-3-(2-propynyl)-2-benzothiazolinone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of 4.7 g of 5-amino-6-fluoro-3-(2-propynyl)-2-benzothiazolinone, 1.93 g of diketene and 0.05 g of 4-pyrrolidinopyridine in 250 ml of benzene is stirred at room temperature for 30 minutes and subsequently held at 50° C. for 30 minutes. In this manner there is obtained a solution of 5-acetoacetylamino-6-fluoro-3-(2-propynyl)-2-benzothiazolinone which is used as such in the next reaction step without isolation of the product.

Workup

  1. waitsubsequently held at 50° C. for 30 minutes

Sources & evidence

ORD record
ord-91a2d8698d2148d7be763773befd8d65
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

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