Phenyl chloroformate → HCID 86622299, compound

HRID 1639567Notes

Reaction equation

HRID 1639567 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([O:12][C:13]1[CH:22]=[CH:21][C:16]2[N:17]=[C:18]([NH2:20])[S:19][C:15]=2[CH:14]=1)(=[O:11])=[O:10].Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:25].C(=O)([O-])O.[Na+]>O1CCCC1.O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:9]([O:12][C:13]1[CH:22]=[CH:21][C:16]2[N:17]=[C:18]([NH:20][C:24]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:25])[S:19][C:15]=2[CH:14]=1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 86622298HCID 86622298, compound

Product 1

HCID 86622299HCID 86622299, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 g of 2-amino-1,3-benzothiazol-6-yl 2,6-dichlorobenzenesulfonate, 3.34 g of phenyl chloroformate, 1.79 g of sodium hydrogen carbonate in 40 cm3 of tetrahydrofuran and 4 cm3 of water is stirred for about 60 hours at a temperature in the region of 20° C. After concentrating the reaction mixture to dryness, the residue is taken up in 20 cm3 of water. The solid is filtered off by suction and washed with twice 5 cm3 of water, and then dried in an oven at 50° C. 2.5 g of 2-[(phenoxycarbonyl)amino]-1,3-benzothiazol-6-yl 2,6-dichlorobenzenesulfonate are thus obtained in the form of a brown solid, the characteristics of which are as follows:

Workup

  1. concentrationAfter concentrating the reaction mixture to dryness
  2. filtrationThe solid is filtered off by suction
  3. washwashed with twice 5 cm3 of water
  4. customdried in an oven at 50° C

Sources & evidence

ORD record
ord-86975376f46b4197a778741011634768
Source dataset
uspto-grants-2012_02
Patent number
US08110571B2

Reaction notes

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