Triethylamine → HCID 24751933, compound

HRID 252243Notes

Reaction equation

HRID 252243 reaction equation
[N-]=C=O.[C:4]1([CH3:17])[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]([NH2:16])=[O:15])(=[O:12])=[O:11])=[CH:6][CH:5]=1.Cl.N[C:20]1[S:21][C:22]([Br:25])=[CH:23][N:24]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:25][C:22]1[S:21][C:20]([NH:16][C:14]([NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([CH3:17])=[CH:9][CH:8]=2)(=[O:11])=[O:12])=[O:15])=[N:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 221703925-Bromo-1,3-thiazol-2-amine--hydrogen chloride (1/1)HCID 86616716Toluene-4-sulfonylurea isocyanate

Product 1

HCID 24751933HCID 24751933, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of toluene-4-sulfonylurea isocyanate (2.6 g, 13 mmol) in CH2Cl2 (10 ml) was added slowly to a mixture containing 2-amino-5-bromothiazole hydrochloride (3.4 g, 13 mmol) and triethylamine (5.4 ml, 39 mmol) in CH2Cl2 (60 ml) under an argon atmosphere and stirred overnight at rt. The reaction mixture was concentrated under reduce pressure, diluted with ethyl acetate and washed with NaHCO3 (half sat. 3×), 5% KHSO4/10% K2SO4, water, NaCl sat., dried (MgSO4.2H2O), filtered and concentrated under reduced pressure. Recrystallization from MeOH/water yielded a beige solid: 2.8 g (58%), MS: m/e 376.1 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with NaHCO3 (half sat. 3×), 5% KHSO4/10% K2SO4, water, NaCl sat.
  4. dry with materialdried (MgSO4.2H2O)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallization from MeOH/water
  8. customyielded a beige solid

Sources & evidence

ORD record
ord-de66dd01d4764801b519b2e2fd4230d7
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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