Carbon tetrabromide → HCID 58327488, compound

HRID 708597Notes

Reaction equation

HRID 708597 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[S:9][C:10]([CH2:14]O)=[C:11]([CH3:13])[N:12]=1)([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:18]>ClCCl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[S:9][C:10]([CH2:14][Br:18])=[C:11]([CH3:13])[N:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11205Carbon tetrabromideHCID 23560820Tert-butyl 5-(hydroxymethyl)-4-methylthiazol-2-ylcarbamate

Product 1

HCID 58327488HCID 58327488, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(5-Hydroxymethyl-4-methyl-thiazol-2-yl)-carbamic acid tert-butyl ester (0.3 g) and 1 g of triphenylphosphine polystyrene (1.2 mmol/g) were taken in anhydrous dichloromethane (6 mL) and cooled to 0° C., and carbontetrabromide (0.4 g) added. The mixture stirred for 1 h. at 0° C. room temperature for 2 h. Resin was filtered and washed with 5 mL of dichloromethane, filtrate was concentrated and dried in vacuum give (5-Bromomethyl-4-methyl-thiazol-2-yl)-carbamic acid tert-butyl ester (0.3 g). This was used in the next reaction with no further purification. 1H NMR (400 MHz, Acetone-d6) 4.9 (s, 2H), 2.45 (s, 3H), 1.55 (s, 3H).

Workup

  1. filtrationResin was filtered
  2. washwashed with 5 mL of dichloromethane, filtrate
  3. concentrationwas concentrated
  4. customdried in vacuum

Sources & evidence

ORD record
ord-a9e8a6a2940a4d6c84c1af2bc2174f9a
Source dataset
uspto-grants-2015_11
Patent number
US09175003B2

Reaction notes

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