Water → HCID 21866466, compound

HRID 478956Notes

Reaction equation

HRID 478956 reaction equation
C([C:8]1[S:12][C:11]([CH2:13][NH2:14])=[N:10][C:9]=1[C:15]([NH2:17])=O)(OC(C)(C)C)=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O.C(Cl)[Cl:40]>>[ClH:40].[NH2:14][CH2:13][C:11]1[S:12][CH:8]=[C:9]([C:15]#[N:17])[N:10]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 67045133HCID 67045133, compound

Product 1

HCID 21866466HCID 21866466, compound

Conditions

Temperature
22.5 °C

Procedure

Boc-2-aminomethylthiazole-4-carboxamide (75.0 g, 0.29 mol) was suspended in 524 ml of methylene chloride and, at from −5 to 0° C., admixed with triethylamine (78.9 g, 0.78 mol) and 79.5 g (0.38 mol) of trifluoroacetic anhydride. The mixture was stirred for another 1 h and then allowed to warm to 20-25° C., 1190 ml of water were added and the phases were separated. 160 ml of 5-6 N isopropanolic hydrochloric acid were added to the organic phase, the mixture was heated to the boil for 3 h, stirred at 20-25° C. overnight and cooled to from −5 to 0° C. for 2.5 h, and the solid was filtered off, washed with methylene chloride and dried. This gave 48.1 g of 2-aminomethyl-4-cyanothiazole of an HPLC purity of 99.4 area %, which corresponds to a yield over these two steps of 94.3%.

Workup

  1. customthe phases were separated
  2. addition160 ml of 5-6 N isopropanolic hydrochloric acid were added to the organic phase
  3. temperaturethe mixture was heated to the boil for 3 h
  4. stirringstirred at 20-25° C. overnight
  5. temperaturecooled to from −5 to 0° C. for 2.5 h
  6. filtrationthe solid was filtered off
  7. washwashed with methylene chloride
  8. customdried
  9. customa yield over these two steps of 94.3%

Sources & evidence

ORD record
ord-97076bb9a8304f7ba6ef6f82819a1ed1
Source dataset
uspto-grants-2003_11
Patent number
US06642388B1

Reaction notes

Loading…