Hydrochloric Acid → Ethyl {[6-(4-Fluorophenoxy)-2-benzothiazolyl]amino}methanethioate

HRID 9135

Reaction equation

HRID 9135 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl[C:20]([O:22][CH3:23])=[S:21].Cl.N1C=CC=C[CH:26]=1>>[F:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:1][C:20](=[S:21])[O:22][CH2:23][CH3:26])[S:3][C:4]=3[CH:10]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 554404Methyl chloromethanethioateHCID 219855122-Amino-6-(4-fluorophenoxy)benzothiazole

Product 1

HCID 86588974Ethyl {[6-(4-Fluorophenoxy)-2-benzothiazolyl]amino}methanethioateYield 65%

Procedure

A suspension of 2-amino-6-(4′-fluorophenoxy)-benzothiazole (associated with 2.0 eq of KBr salt, 2.50 g, 5.02 mmol) in 10 mL pyridine was treated dropwise with methyl chlorothioformate (0.65 mL, 7.53 mmol, 01.5 eq). It was stirred at room temperature for about 1 hour, and was poured into 40 mL ice water. The mixture was acidified slowly with 1 M HCl solution. The result precipitate was filtered off, washed with water and MeOH, and dried under vacuum to give 1.18 g (65%) desired compound. LC/MS 334.9 (M+1); LC retention time 3.70 min.

Workup

  1. filtrationThe result precipitate was filtered off
  2. washwashed with water and MeOH
  3. customdried under vacuum

Sources & evidence

ORD record
ord-740e84ce00124f83a802a02af18c14b6
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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