Dimethyl Sulfoxide → HCID 86661312, compound

HRID 1685078Notes

Reaction equation

HRID 1685078 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(C)=O.Cl[CH2:10][C:11]1[N:12]=[C:13]([NH:16][C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)=[O:18])[S:14][CH:15]=1>O>[N:1]([CH2:10][C:11]1[N:12]=[C:13]([NH:16][C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)=[O:18])[S:14][CH:15]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 58055090HCID 58055090, compound2×

Product 1

HCID 86661312HCID 86661312, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium azide (390 mg, 6.0 mmol) was added to a DMSO (5 mL) solution of Intermediate 4: 1-(4-(chloro-methyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea (600 mg, 2 mmol). The mixture was stirred for 4 hours at 40 C. Upon completion of the reaction, water was added at 10 C and the mixture was extracted with EtOAc. Organics were washed with brine, dried and evaporated. Recrystallization from CH2Cl2/hexane afforded 1-(4-(azidomethyl)thiazol-2-yl)-3-(3-fluorobenzyl)urea. 1H NMR (400 MHz, CDCl3): δ 10.3 (1H, br), 7.27 (m, 1H), 7.1-6.9 (m, 3H), 6.74 (s, 1H), 4.50 (d, 2H), 4.27 (s, 2H). MS (ES+): M/Z 307 (M+H)+.

Workup

  1. additionwas added at 10 C
  2. extractionthe mixture was extracted with EtOAc
  3. washOrganics were washed with brine
  4. customdried
  5. customevaporated
  6. customRecrystallization from CH2Cl2/hexane

Sources & evidence

ORD record
ord-2cdc62425465411e94ec9c7673b10ae2
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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