Bromine → 1-(5-Bromo-6-methoxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

HRID 712181Notes

Reaction equation

HRID 712181 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[Br:18]Br>C(Cl)Cl.CO>[Br:18][C:13]1[C:14]([O:16][CH3:17])=[CH:15][C:9]2[S:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[N:11][C:10]=2[CH:12]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 168004671-Ethyl-3-(6-methoxy-1,3-benzothiazol-2-yl)urea

Product 1

HCID 596030851-(5-Bromo-6-methoxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(6-methoxy-1,3-benzothiazol-2-yl)urea (1.10 g, 4.38 mmol) was suspended in DCM (50 mL) and MeOH (5 mL). Bromine (0.34 mL, 6.60 mmol) was added and the mixture stirred at rt. The mixture was stirred for a total of 1.5 h then concentrated to dryness under reduced pressure. The desired compound was obtained as an orange solid, 2.17 g, and used without further purification, stating purity as 66 mass % in further reactions. m/z: 329.94/331.91 [M+H]+.

Workup

  1. stirringThe mixture was stirred for a total of 1.5 h
  2. concentrationthen concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9fad3ba92a704b7a878436ca2e54f259
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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