Hydrochloric Acid → HCID 87471201, compound

HRID 220735Notes

Reaction equation

HRID 220735 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]2[CH2:13][CH:12](C(O)=O)[CH2:11][CH2:10][C:8]=2[N:9]=1)(=[O:3])[CH3:2].C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[ClH:41].CN(C)[CH:44]=[O:45]>CO>[ClH:41].[CH3:44][O:45][C:22](=[O:31])[NH:19][CH:12]1[CH2:11][CH2:10][C:8]2[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=2[CH2:13]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2×HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11593905HCID 11593905, compound

Product 1

HCID 87471201HCID 87471201, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 ml reactor equipped with mechanical stirrer, thermometer and condenser is loaded with 5 g of 2-acetylamino-4,5,6,7-tetrahydro-benzothiazole-6-carboxylic acid [(I), R=—NH—CO—CH3] suspended in 80 ml of N,N-dimethylformamide; then 2.32 g of triethylamine are added. A solution consisting of 6.3 g of diphenylphosphoryl azide (DPPA) dissolved in 7 ml N,N-dimethylformamide is dropped therein in 2 hours. The reaction mixture gradually solubilizes during the addition until complete dissolution. After 6 hours the reaction solution is dropped in 1 liter of a methanol solution containing 8 ml of 37% hydrochloric acid at 60° C. The mixture is left to cool, then extracted twice with 100 ml of methylene chloride, discarding the organic phase. The aqueous phase is concentrated to a residue that is crystallized from i-propanol-water to obtain 3.6 g of a white solid.

Workup

  1. customA 500 ml reactor equipped with mechanical stirrer
  2. additionis dropped
  3. additionThe reaction mixture gradually solubilizes during the addition until complete dissolution
  4. waitThe mixture is left
  5. temperatureto cool
  6. extractionextracted twice with 100 ml of methylene chloride
  7. concentrationThe aqueous phase is concentrated to a residue that
  8. customis crystallized from i-propanol-water

Sources & evidence

ORD record
ord-59ca4b2eb40a4b52aff57f6d8cac9f67
Source dataset
uspto-grants-2012_06
Patent number
US08203002B2

Reaction notes

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